Tag: 200-300

Synthesis, Properties, and Solar Cell Performance of Poly(4-(p-alkoxystyryl)thiazole)s was written by Jaeger, Jakob;Schraff, Sandra;Pammer, Frank. And the article was included in Macromolecular Chemistry and Physics in 2018.Safety of 5-Bromo-4-methyl-thiazol-2-ylamine hydrobromide The following contents are mentioned in the article:

Polythiazoles (PvTzs) featuring conjugated styryl sidechains equipped with different solubilizing p-alkoxy-groups (-OR, R = n-octyl, n-dodecyl, 2-ethylhexyl, 2-hexyldecyl) is prepared by Negishi-coupling polycondensation. Soluble material with number-average mol. weights of up to M_n = 8.5 kDa (polydispersity (PDI) = 1.3, d.p. (DPn) ≈ 20) is obtained, with a head-to-tail content of the PvTzs of ≈77%, as estimated from comparison with reference polymers. The polymers exhibit optical absorption properties similar to their polythiophene analogs, while their electrochem. characterization shows a significant stabilization of their frontier orbital levels. Fluorescence measurements indicate that upon excitation of the electron rich alkoxystyryl side-chains charge transfer onto the more electron deficient polythiazole backbone occurs. This finding is corroborated by d. functional theory (DFT) calculations on oligomeric model systems, which also consistently reproduce the optical properties observed for the polymers. The potential of these materials for applications in organic electronics can be demonstrated by their use as donor materials in organic photovoltaic cells, which exhibit higher open circuit voltages (V_OC, up to 0.86 V) than P3HT- or analogous polythiophene-based cells (V_OC = 0.5-0.6 V). This study involved multiple reactions and reactants, such as 5-Bromo-4-methyl-thiazol-2-ylamine hydrobromide (cas: 79247-77-1Safety of 5-Bromo-4-methyl-thiazol-2-ylamine hydrobromide).

5-Bromo-4-methyl-thiazol-2-ylamine hydrobromide (cas: 79247-77-1) belongs to thiazole derivatives. Thiazole rings are planar and aromatic. Thiazoles are characterized by larger pi-electron delocalization than the corresponding oxazoles and have therefore greater aromaticity. The pyridine-type nitrogen in the thiazole ring deactivates the ring for electrophilic substitution reactions, which is further reduced in acid due to protonation of the thiazole ring.Safety of 5-Bromo-4-methyl-thiazol-2-ylamine hydrobromide

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

QSAR study on H₃-receptor affinity of benzothiazole derivatives of thioperamide was written by Bordi, Fabrizio;Mor, Marco;Morini, Giovanni;Plazzi, Pier Vincenzo;Silva, Claudia;Vitali, Tullo;Caretta, Antonio. And the article was included in Farmaco in 1994.Application In Synthesis of 6-Butoxybenzo[d]thiazol-2-amine The following contents are mentioned in the article:

Starting from the structure of thioperamide, a known H₃-antagonist, a new series of compounds I (R = H, NO₂, Br, etc.) with a benzothiazole nucleus instead of the cyclohexylcarbothioamide moiety was synthesized. Various substituents, selected by exptl. design, were introduced in position 6 of the benzothiazole nucleus, in order to change its physico-chem. characteristics. The lipophilicity of the synthesized compounds was measured by means of RP-HPLC, and their H₃-receptor affinity was evaluated by competitive binding assays on rat cortex synaptosomes, with the labeled ligand N^α-[³H]methylhistamine. A QSAR anal. was performed on the exptl. data, using also substituent constants taken from the literature. The newly synthesized compounds showed lower H₃-affinities than thioperamide; quant. structure-activity relationships, described by models obtained with PLS and MRS techniques, were observed among benzothiazole derivatives According to these relationships, any attempt to improve the potency of these compounds should involve the substitution of the benzothiazole moiety with less bulky and/or more flexible structures, which should also be less lipophilic and allow better electronic interactions with the binding site. 1-(Benzothiazol-2-yl)-4-[(1H)-imidazol-4-yl]piperidine represents a limit structure for H₃-activity, since it seems impossible to improve its affinity by means of substitution in the studied position of the benzothiazole nucleus, as shown by predictions performed by a PLS model. This study involved multiple reactions and reactants, such as 6-Butoxybenzo[d]thiazol-2-amine (cas: 14372-65-7Application In Synthesis of 6-Butoxybenzo[d]thiazol-2-amine).

6-Butoxybenzo[d]thiazol-2-amine (cas: 14372-65-7) belongs to thiazole derivatives. Thiazole rings are planar and aromatic. Thiazoles are characterized by larger pi-electron delocalization than the corresponding oxazoles and have therefore greater aromaticity. Thiazole is a versatile building block for the construction and lead generation of new drug discoveries. Numerous diazole-based compounds are in clinical use as anticancer, antileukemic, antiinflammatory, antiviral, antifungal, antirheumatic, immunomodulator, and antiparasitic agents.Application In Synthesis of 6-Butoxybenzo[d]thiazol-2-amine

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Synthesis and Evaluation of Novel Radioligands for Positron Emission Tomography Imaging of Metabotropic Glutamate Receptor Subtype 1 (mGluR1) in Rodent Brain was written by Fujinaga, Masayuki;Yamasaki, Tomoteru;Yui, Joji;Hatori, Akiko;Xie, Lin;Kawamura, Kazunori;Asagawa, Chiharu;Kumata, Katsushi;Yoshida, Yuichiro;Ogawa, Masanao;Nengaki, Nobuki;Fukumura, Toshimitsu;Zhang, Ming-Rong. And the article was included in Journal of Medicinal Chemistry in 2012.Quality Control of 4-(6-Chloropyrimidin-4-yl)-N-methylthiazol-2-amine The following contents are mentioned in the article:

Three novel positron emission tomog. ligands, N-(4-(6-(isopropylamino)pyrimidin-4-yl)-1,3-thiazol-2-yl)-4-[¹¹C]methoxy-N-methylbenzamide ([¹¹C]I), 4-[¹⁸F]fluoroethoxy-N-[4-[6-(isopropylamino)pyrimidin-4-yl]-1,3-thiazol-2-yl]-N-methylbenzamide ([¹⁸F]II), and 4-[¹⁸F]fluoropropoxy-N-[4-[6-(isopropylamino)pyrimidin-4-yl]-1,3-thiazol-2-yl]-N-methylbenzamide ([¹⁸F]III), were designed for imaging metabotropic glutamate receptor type 1 (mGluR1) in rodent brain. Unlabeled compound I was synthesized by benzoylation of 4-pyrimidinyl-2-methylaminothiazole, followed by reaction with isopropylamine. Removal of the Me group in I gave the phenol precursor for radiosynthesis. Two fluoroalkoxy analogs II and III were prepared by reacting the phenol with the corresponding fluorine-containing tosylates. Radioligands [¹¹C]I, [¹⁸F]II, and [¹⁸F]III were synthesized by O-[¹¹C]methylation or [¹⁸F]fluoroalkylation of the phenol precursor. Compound I showed high in vitro binding affinity for mGluR1, whereas II and III had weak affinity. Autoradiog. using rat brain sections showed that [¹¹C]I binding is aligned with the reported distribution of mGluR1 with high specific binding in the cerebellum and thalamus. PET study with [¹¹C]I in rats showed high brain uptake and a similar distribution pattern to that in autoradiog., indicating the usefulness of [¹¹C]I for imaging brain mGluR1. This study involved multiple reactions and reactants, such as 4-(6-Chloropyrimidin-4-yl)-N-methylthiazol-2-amine (cas: 932738-80-2Quality Control of 4-(6-Chloropyrimidin-4-yl)-N-methylthiazol-2-amine).

4-(6-Chloropyrimidin-4-yl)-N-methylthiazol-2-amine (cas: 932738-80-2) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). There are numerous natural products that possess a thiazole ring with broad pharmacological activities. Thiamine, also known as vitamin B1, possesses a thiazole ring linked with 2-methylpyrimidine-4-amine as hydrochloride salt.Quality Control of 4-(6-Chloropyrimidin-4-yl)-N-methylthiazol-2-amine

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Antituberculous compounds. V. 2-Sulfanilamido-5-alkyl-1,3,4-oxadiazoles and -thiadiazoles and related isothiosemicarbazones and isothioureas was written by Brooks, J. D.;Charlton, P. T.;Macey, P. E.;Peak, D. A.;Short, W. F.. And the article was included in Journal of the Chemical Society in 1950.Application In Synthesis of 6-Butoxybenzo[d]thiazol-2-amine The following contents are mentioned in the article:

This work arose out of the observation that 2-sulfanilamido-5-methyl-1,3,4-oxadiazole (I), although virtually inactive against organisms normally sensitive to sulfonamides, exhibited a highly sp. activity in vitro against Mycobacterium tuberculosis. N⁴-Acyl derivatives of I were prepared from the acid anhydride in C₆H₆ (hexanoyl, m. 203°) or with the acid chloride in C₅H₅N (dodecanoyl, m. 124°; stearoyl, m. 128-9°). I(2.5g.)in 15 cc. H₂O and 4cc. concentrated HCl, treated with 3.3 g. iodine monochloride in 3 cc. concentrated HCl, gives 3 g. 2-(3,5-diiodosulfanilamido)-5-methyl-1,3,4-oxadiazole, m. 228-9°. 1-Acylthiosemicarbazones were prepared with the appropriate acid anhydride at 80° and finally at 110-20°; 10 g. of the crude product and 3 mols. PbO, heated 15-30 hrs. in 150-200 cc. EtOH, give the 5-alkyl derivatives of 2-amino-1,3,4-oxadiazole: 5-Am, m. 151° (N-sulfanilyl derivative, m. 148-9°; N⁴-Ac derivative, m. 186°); 5-hendecyl, m. 150-1° (N-sulfanilyl derivative, m. 105-7°); 5-heptadecyl, m. 143° (N-sulfanilyl derivative, m. 91-3°). 2-(p-Tolylsulfonamido)-5-methyl-1,3,4-oxadiazole, m. 152°. 1-Hexanoylthiosemicarbazide (22 g.) and 30 g. PhSO₃H, heated 15 min. on the steam bath and the aqueous solution basified with NH₄OH, give 17 g. 2-amino-5-amyl-1,3,4-thiadiazole, m. 195°; 2-sulfanilamido analog, m. 182° (N⁴-Ac derivative, m. 201-2°). In view of the unfavorable in vivo properties of the above compounds, a series of 3-alkylisothiosemicarbazones (II) and 2-alkylisothioureas was prepared p-BuOC₆H₄NCS (III) (4.25 g.) in 6 cc. absolute EtOH, treated with 1.2 cc. 90% N₂H₄.H₂O in 1 cc. EtOH and the crude product refluxed 3 hrs. with 2.2 g. BzH in 60 cc. EtOH, gives 4.5 g. benzaldehyde 4-p-butoxyphenylthiosemicarbazone, pale yellow, m. 164-5°. The II were prepared from the corresponding thiosemicarbazones by alkylation with EtONa and the appropriate alkyl halide in EtOH. Acetone 3-ethylisothiosemicarbazone (IV) HCl salt m. 153-4°; 3.2 g. IV and 2.1 g. NaHCO₃ in 25 cc. 50% EtOH, treated with 5.13 g. p-AcNHC₆H₄SO₂Cl, give 0.67 g. of the 4-(N-acetylsulfanilyl) derivative (V), m. 183-4°; 0.17 g. V and 1 cc. 2.5 N NaOH, heated 1 hr. at 100°, give 0.14 g. of the 4-sulfanilyl derivative, m. 186-7°. Benzaldehyde 3-butylisothiosemicarbazone HCl salt, m. 185-6°; 3-octyl homolog HCl salt, m. 176°; 3-hexadecyl homolog HCl salt, m. 162-3°; 3-(2-diethylaminoethyl) analog di-HCl salt, m. 192°. Benzaldehyde 4-phenyl-3-ethylisothiosemicarbazone (VA), pale yellow m. 78°; the 3-(2-diethylaminoethyl) analog forms a reineckate, m., 166-7° (decomposition). 4-(p-Butoxyphenyl) analog of VA, m. 90°. p-1-Pyrrolidylbenzaldehyde 3-ethylisothiosemicarbazone HCl salt, reddish brown, m. 245° (decomposition). p-Dimethylaminobenzaldehyde 3-ethylisothiosemicarbazone di-HCl salt, yellow, m. 219-20° (decomposition); boiling EtOH gives the mono-HCl salt, red, m. 230-2°. 2-Nitrobenzaldehyde analog HCl salt m. 169.5-70.5°. The S-alkylisothioureas were prepared from the appropriate thiourea and alkyl halides in boiling EtOH: N-phenyl-S-ethyl (VI) (picrate, yellow, m. 199.5°); S-Bu homolog (picrate, yellow, m. 144°); S-octyl homolog (picrate, yellow, m. 130.5°). N-p-Butoxyphenyl analog of VI (picrate, yellow, m. 162-3°); S-Bu homolog, (HI salt, m. 109-10°); S-octyl homolog (HBr salt, m. 96-6.5°). The activities of the thiadiazoles and the thiosemicarbazones are entirely unrelated. The low activity of the S-alkylisothioureas in the serum precluded in vivo activity. 2-Mercaptobenzimidazole and EtI, refluxed 2 hrs. in EtOH, give the 2-ethylmercapto analog m. 173.5-4.5°. p-BuOC₆H₄NH₂ (8.25 g.) and 9.5 g. NH₄NCS in 50 cc. 95% AcOH, treated with 10 g. Br in 13 cc. AcOH and kept overnight, give 2.2 g. 2-amino-6-butoxybenzothiazole, m. 119°. 2-Chloro-6-nitrobenzothiazole (10 g.) in 250 cc. BuOH, refluxed 20 hrs. with 1.07 g. Na in 50 cc. BuOH, give 4.15 g. 6-nitro-2-butoxybenzothiazole (VII), m. 60°; 10 g. VII, added in portions to 32 g. SnCl₂.₂H₂O in 40 cc. concentrated HCl at 70-80° and finally refluxed 30 min., gives 2.5 g. x-chloro-6-amino-2-butoxybenzothiazole-2HCl, m. 268° (decomposition). In the preparation of 2-mercapto-4-phenyl-6-methylpyrimidine (VIII), the fraction insoluble in EtOH, dilute HCl, or NaOH is bis(4-phenyl-6-methyl-2-pyrimidyl) disulfide, yellow, m. 185.5-6°; it results on oxidation of VIII in dilute NaOH with aqueous iodine. The appropriate S-alkylisothiourea-HX in 1 equivalent 2.5 N NaOH, treated with 1 mol. crude Et sodioformylpropionate, gives a 4-hydroxy-2-alkylmercapto-5-methylpyrimidine; with PCl₅ and POCl₃ (refluxed 45 min.) they give the 4-Cl compounds; these give the 4-NH₂ compounds when heated 6-8 hrs. with 8-10 parts (by weight) 10% EtOH-NH₃ at 135-50°. The following pyrimidines are reported: 2-methylmercapto-4-phenyl-6-methyl, b₁ 154-60°; 4-hydroxy-2-butylmercapto-5-methyl, m. 105-6°; 2-octylmercapto analog, m. 88-9°; 4-chloro-2-methylmercapto-6-methyl, b₁₅ 132°, m. 20-3°; 4-chloro-2-butylmercapto-5-methyl, b₁ 124-6°; octylmercapto homolog, b₂ 144-8°; 4-amino-2-methylmercapto-5-methyl, m. 130-1°; butylmercapto homolog, m. 85-6°; octylmercapto homolog, m. 85-6°. In no case were the compounds active at a dilution greater than 1:1000 in the presence of serum. This study involved multiple reactions and reactants, such as 6-Butoxybenzo[d]thiazol-2-amine (cas: 14372-65-7Application In Synthesis of 6-Butoxybenzo[d]thiazol-2-amine).

6-Butoxybenzo[d]thiazol-2-amine (cas: 14372-65-7) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1).Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Application In Synthesis of 6-Butoxybenzo[d]thiazol-2-amine

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Syntheses of heterocyclic compounds of nitrogen. CV. Benzothiazole derivatives. 9 was written by Takahashi, Torizo;Okada, Jutaro;Yamamoto, Yasuo. And the article was included in Yakugaku Zasshi in 1957.Category: thiazole The following contents are mentioned in the article:

A mixture of 12 g. 3-ClC₆H₄NH₂, 15 g. NH₄SCN, and 75 ml. AcOH at 5° treated dropwise with 16 g. Br in 32 g. AcOH, the product diluted with 4 volumes H₂O, neutralized with Na₂CO₃, the precipitate filtered off, taken up in 10% HCl, the HCl layer made alk. with NH₄OH, and the product recrystallized from C₆H₆ gave 6 g. 3,4-Cl(NCS)C₆H₃NH₂ (I), columns, m. 75°. Or, reducing 0.6 g. 3,4-Cl(NCS)C₆H₃NO₂ in 6 ml. concentrated HCl with 6 g. SnCl₂.2H₂O, suspending the precipitate in H₂O, alkalinizing with NaOH, and extracting with Et₂O gave C₆H₆-soluble I and C₆H₆-insoluble [2,4-Cl(H₂N)C₆H₃]₂S₂, m. 136-8°. 3-ClC₆H₄NHCSNH₂ (50 g.) in 150 ml. CHCl₃ treated dropwise with 44 g. Br in 30 ml. CHCl₃, heated 1 hr. on an H₂O bath, the solvent removed, the residue in 800 ml. H₂O and 5 ml. 48% HBr treated with a small amount of Na₂SO₃, made alk. with Na₂CO₃, and the precipitate recrystallized from dilute EtOH gave 28 g. 2-amino-5-chlorobenzothiazole (II), needles, m. 198°; the filtrate from II made alk. with K₂CO₃ and the precipitate recrystallized from dilute EtOH gave 16.5 g. 7-Cl analog (III) of II, needles, m. 145-50°. Or, the reduction of 0.6 g. 5,2-Cl(NCS)C₆H₃NO₂ with 6 g. SnCl₂.2H₂O gave 0.4 g. II, m. 196-8°. A mixture of 1 mole RC₆H₃.S.C(NH₂):N [R = 6-MeO (IIIA), 6-EtO (IV), 6-BuO (V), 4-Cl (VI), 5-Cl (VII), or 6-Cl (VIII)] (2 moles used in the case of III) in CHCl₃, 1 mole C₅H₅N (no addition in the case of III), and 1 mole 2-bromoacyl bromide or (ClCH₂CO)₂O heated 0.5-1 hr. on an H₂O bath, the solvent removed, and the product recrystallized from solvent gave RC₆CH₃.S.C(NHCOCHXR¹):N (IX) (R, R¹, X, and m.p. given): IIIA, H, Br, 164-5°; III, Me, Br, 148°; III, Et, Br, 123°; III, Me₂CH, Br, 128-8.5°; IV, H, Cl, 181°; IV, Me, Br, 145°; IV, Et, Br, 139°; IV, Me₂CH, Br, 115°; V, H, Br, 162-3°; V, Me, Br, 122°; V, Et, Br, 99-100°; V, Me₂CH, Br, 129°; VI, Me, Br, 152°; VII, H, Br, 178°; VII, Me, Br, 160°; VII, Et, Br, 182-3°; VII, Me₂CH, Br, 156-7°; VIII, H, Cl, 218°; VIII, Me, Br, 149°; VIII, Et, Br, 146°; VIII, Me₂CH, Br, 150°. A mixture of 1 mole IX and a C₆H₆ solution containing more than 2 moles Me₂NH in a sealed tube heated 1 hr. at 100°, kept overnight, and the solvent removed gave RC₆H₃.S.C(NHCOCHR¹NMe₂):N (X) (R, R¹, and m.p. given): III, H, 113-14°; III, Me, 113°; IV, H, 126° (as HCl salt); IV, Me, 178° (picrate); IV, Et, 91°; V, H, 96-7°; V, Me, 76-7°; VI, Me, 106-7°; VII, H, 144-5°; VII, Me, 163-4°; VII, Et, 120-1°; VIII, H, 136°; VIII, Me, 255° (decomposition) (as HCl salt); VIII, Et, 260° (decomposition) (as HCl salt). This study involved multiple reactions and reactants, such as 6-Butoxybenzo[d]thiazol-2-amine (cas: 14372-65-7Category: thiazole).

6-Butoxybenzo[d]thiazol-2-amine (cas: 14372-65-7) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. The nitrogen in thiazole is sp2 hybridized and the lone pair of electrons localized on the nitrogen is less reactive due to increased aromatic character and decreased basicity. It is protonated and alkylated/acylated at nitrogen forming hydrochloride and quaternary thiazolium salt.Category: thiazole

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Organic thiocyanates. XIX. Thiocyanation of phenol ethers was written by Pohloudek-Fabini, Roland;Luess, K. D.. And the article was included in Archives de Pharmacie (Paris) in 1966.Computed Properties of C11H14N2OS The following contents are mentioned in the article:

Thiocyanation of alkyl phenyl ethers with inorganic thiocyanates and Br gave low yields of thiocyanates because bromination occurred simultaneously. Alkyl aminophenyl ethers yielded mixtures of mono and dithiocyanato derivatives When heated or treated with acids, the o-aminothiocyanato derivatives isomerized to 2-aminobenzothiazoles. Unsubstituted alkyl thiocyanatophenyl ethers were prepared from the corresponding aminophenyl ethers by diazotization and treatment with KSCN, CuSCN, and CoCl2. Phenol ethers (0.1 mole) and 0.3 mole NaSCN or KSCN in AcOH, 100 g. NH4SCN in MeOH, or 0.5 mole NaSCN or KSCN in AcOMe were cooled and treated with 0.2 mole Br in the same solvent (compound used, product(s), m.p., and % yield in AcOH, MeOH, and AcOMe listed): PhOMe, 4-MeOC6H4SCN, 34-5°, 12, 0, -; PhOEt, 4-EtOC6H4SCN, 46-7.5°, 17, 0, -; PhOPr, 4-PrOC6H4SCN, 36-6.5°, 17, 0, -; PhOBu, 4-BuOC6H4SCN, 26-7°, 15, 0, -; o-anisidine, 1,2,5-MeO(H2N)C6H3SCN, 52-3°, 68, 41, 92; 1,2,3,5-MeO(H2N)C6H2(SCN)2, 101-3° and 233° (twice), 28, 56, 0, and 4-methoxy-6-thiocyanato-2-aminobenzothiazole, 233-5° (decomposition), 60, 0, 0; m-anisidine, 1,3,6-MeO(H2N)C6H3SCN, 109-11°, 39, 2, 22, and 1,3,4,6-MeO(H2N)C6H2(SCN)2, 155-7°, 84, 75, 47; p-anisidine, 1,4,3-MeO(H2N)C6H3SCN, 61-2 and 168°, 0, 0, 25, 6-methoxy-2-aminobenzothiazole, 169°, 91, 3, 3, and 6-methoxy-4-thiocyanato-2-aminobenzothiazole, 212-16° (decomposition), 15, 72, 0; o-phenetidine, 1,2,5-EtO(H2N)C6H3SCN, 82-3°, 79, 53, 75, and 1,2,3,5-EtO(H2N)C6H2(SCN)2, 103-6° and 228°, 30, 80, 0; m-phenetidine, 1,3,4,6-EtO(H2N)C6H2(SCN)2, 105-7.5°, 100, 100, 92; p-phenetidine, 1,4,3-EtO(H2N)C6H3SCN, 70-2 and 164°, 0, 0, 31, 6-ethoxy-2-aminobenzothiazole, 164-6, 89, 42, 0, and 6-ethoxy-4-thiocyanato-2-aminobenzothiazole, 206-12° (decomposition), 5, 31, 0; 1,4-PrOC6H4NH2, 6-propoxy-2-aminobenzothiazole, 137-9°, 67, 22, -; 1,4-BuOC6H4NH2, 6-butoxy-2-aminobenzothiazole, 120-1°, 26, 15, -. Thiocyanates prepared by diazotization were (starting material, product, m.p., and % yield listed): o-anisidine, 1,2-MeOC6H4SCN, – (b14 151-2°), 39; m-anisidine, 1,3-MeOC6H4SCN, – (b8 151-2°), 40; p-anisidine, 1,4-MeOC6H4SCN, 33-4°, 29; o-phenetidine, 1,2-EtOC6H4SCN, 23-4° (b7 122-31°), 14; m-phenetidine, 1,3-EtOC6H4SCN, – (b9 138-42°), 42; p-phenetidine, 1,4-EtOC6H4SCN, 44-6°, 17; 1,4-PrOC6H4NH2, 1,4-PrOC6H4NH2, 1,4-PrOC6H4SCN, 34-6° (b6 145°), 20; 1,4-BuOC6H4NH2, 1,4-BuOC6H4SCN, 25-6°, 25; 1,2,5-MeO(H2N)C6H3SCN, 1,2,5-MeOC6H3(SCN)2, 89-93.5°, 29; 1,2,3,5-MeO(H2N)C6H2(SCN)2, 1,2,3,5-MeOC6H2(SCN)3, 129-34°, 59; 1,3,4,6-MeO(H2N)C6H2(SCN)2, 1,3,4,6-MeOC6H2(SCN)3, 114-18.5°, 90 (putative); 1,3,4,6-EtO(H2N)C6H2(SCN)2, 1,3,4,6-EtOC6H2(SCN)3, 115-19°, 100 (putative); 4-methoxy-6-thiocyanato-2-aminobenzothiazole, 4-methoxy-2,6-dithiocyanobenzothiazole, 125-8°, 43; 6-methoxy-2-aminobenzothiazole, 6-methoxy-2-thiocyanobenzothiazole, 86-7°, 30; 6-ethoxy-2-aminobenzothiazole, 6-ethoxy-2-thiocyanatobenzothiazole, 84-8°, 80; 1,2,5-EtO(H2N)C6H3SCN, 1,2,5-EtOC6H3(SCN)2, 52-7°, 80 (putative). This study involved multiple reactions and reactants, such as 6-Butoxybenzo[d]thiazol-2-amine (cas: 14372-65-7Computed Properties of C11H14N2OS).

6-Butoxybenzo[d]thiazol-2-amine (cas: 14372-65-7) belongs to thiazole derivatives. The higher aromaticity of thiazole is due to delocalization of a lone pair of sulfur electrons across the ring, which is evidenced by chemical shifts of ring hydrogen at δ 7.27 and 8.77 ppm (C2 and C4), indicating diamagnetic ring current. Electrophilic attack at nitrogen depends on the presence of electron density at nitrogen as well as the position and nature of substituent linked to the thiazole ring.Computed Properties of C11H14N2OS

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Synthesis of some 4-alkoxy- and 6-alkoxy-2-benzo-thiazolylamides was written by Mndzhoyan, A. L.;Azaryan, A. S.;Iradyan, M. A.;Aroyan, A. A.. And the article was included in Azerbaidzhanskii Khimicheskii Zhurnal in 1967.Application In Synthesis of 6-Isopropoxybenzo[d]thiazol-2-amine The following contents are mentioned in the article:

o- and p-Alkoxynitrobenzenes are hydrogenated over Ni-Cr2O3 to give o- and p-alkoxyanilines (I). Treating I with KSCN and Br gave the corresponding II and III, resp., which were converted into the corresponding amides (IV) and (V), resp. Thus, a mixture of 0.3 mole alkoxynitrobenzene, 50 cc. EtOH, and 4 g. Ni-Cr2O3 catalyst was hydrogenated in an autoclave at 110-20°/100 atm. for 10-12 hrs., filtered, and distilled to give 74.8-86.3% I. From I the following II and III were prepared (R, m.p., m.p. hydrochloride, and % yield given): 6-Et, 159-60°, 199-200°, 60.9; 4-Et, 76-8°, 176-8°, 51.9; 6-Pr, 127-9°, 189-90°, 86.5; 6-iso-Pr, 158-9°, 191-3°, 80.2; 4-Pr, 114-15°, 160-1°, 51.2; 6-Bu, 119-21°, 140-1°, 89.6; 6-iso-Bu, 160-1°, 189-91°, 69.1. A mixture of 0.05 mole acyl chloride and 150 cc. 1:1 Me2CO-dioxane placed in a flask connected with extractor in which a paper extraction shell containing 0.1 mole II or III was placed, was heated on a water bath to complete solution of II or III, filtered, washed with Me2CO, and crystallized from EtOH to obtain the following IV (R, R1, m.p., and % yield given): Et, iso-PrCO, 91-2°, 45.5; Et, Bz, 109-10°, 80.5; Et, MeOC6H4CO (A), 120-2°, 85.3; Et, EtOC6H4CO (B), 116-18°, 76; Et, PrOC6H4CO (C), 94-7°, 84.1; Et, iso-PrOC6H4CO (D), 94-6°, 84.2; Et, BuOC6H4CO (E), 97-8°, 81; Et, PhSO2 (F), 155-7°, 87.4; Et, 2-furoyl (G), 129-30°, 83.3; Et, 2-benzofuroyl (H), 152-4°, 71.8; Et, 2-(2,3-dihydrobenzofuroyl) (I), 110-12°, 70.6; Pr, EtC6H4CO, 191-2°, 79; Pr, G, 224-5°, 80.9; Pr, I, 169-70°, 79.1; and the following V (same data): Et, PrCO, 172-3°, 53.3; Et, iso-PrCO, 140-1°, 45.4; Et, Bz, 222-5°, 87.2; Et, A, 198-200°, 86.9; Et, B, 212-13°, 70.1; Et, C, 224-6°, 84.7; Et, D, 197-200°, 73; Et, F, 199-202°, 60.1; Et, E, 202-3°, 68; Et, iso-BuOC6H4CO, 221-2°, 60; Et, G, 158-9°, 51.9; Et, H, 216-17°, 64.6; Et, I, 142-3°, 90.5; Pr, Bz, 220-2°, 69.2; Pr, A, 145-6°, 80; Pr, B, 204-6°, 86.8; Pr, C, 192-4°, 81.1; Pr, D, 189-90°, 91.8; Pr, E, 197-8°, 67.9; Pr, F, 200-2°, 85.4; Pr, G, 151-2°, 79.5; Pr, H, 212-13°, 65.3; Pr, I, 120-1°, 73.4; iso-Pr, iso-PrCO, 136-9°, 40.3; iso-Pr, BuCO, 138-40°, 49; iso-Pr, Bz, 225-6°, 83.7; iso-Pr, A, 228-9°, 73.1; iso-Pr, B, 215-16°, 60; iso-Pr, F, 255-6°, 68.8; iso-Pr, G, 181-4°, 58.6; Bu, BuCO, 140-1°, 70.6; Bu, Bz, 184-6°, 84.6; Bu, A, 181-2°, 50.1; Bu, B, 182-4°, 81.1; Bu, E, 195-7°, 69.8; Bu, H, 158-60°, 76.5; iso-Bu, A, 222-3°, 85.1; Et, ClCH2CO, 170-1°, 81.4; Bu, ClCH2CO, 172-3°, 70.4. A mixture of 0.03 mole Et2NH, 25 cc. EtOH, 0.01 mole (N-6-alkoxy-2-benzothiazolyl)-2-chloroacetamide, and 25 cc. EtOH was heated on a water bath 2-3 hrs., EtOH was distilled, the residue alkalized with 10% NaHCO3 and extracted with Et2O, the extract dried with Na2SO4 and distilled to give the corresponding V: (R, R1, b.p./mm., m.p., and % yield given): Et, Et2NCH2CO, 218-20°/5, 90-2°, 31.9; Bu, Et2NCH2CO, 130-3°/5, 121-2°, 48.3. This study involved multiple reactions and reactants, such as 6-Isopropoxybenzo[d]thiazol-2-amine (cas: 15850-81-4Application In Synthesis of 6-Isopropoxybenzo[d]thiazol-2-amine).

6-Isopropoxybenzo[d]thiazol-2-amine (cas: 15850-81-4) belongs to thiazole derivatives. Thiazole rings are planar and aromatic. Thiazoles are characterized by larger pi-electron delocalization than the corresponding oxazoles and have therefore greater aromaticity. The nitrogen in thiazole is sp2 hybridized and the lone pair of electrons localized on the nitrogen is less reactive due to increased aromatic character and decreased basicity. It is protonated and alkylated/acylated at nitrogen forming hydrochloride and quaternary thiazolium salt.Application In Synthesis of 6-Isopropoxybenzo[d]thiazol-2-amine

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Synthesis of some 4-alkoxy- and 6-alkoxy-2-benzo-thiazolylamides was written by Mndzhoyan, A. L.;Azaryan, A. S.;Iradyan, M. A.;Aroyan, A. A.. And the article was included in Azerbaidzhanskii Khimicheskii Zhurnal in 1967.Name: 6-Butoxybenzo[d]thiazol-2-amine The following contents are mentioned in the article:

o- and p-Alkoxynitrobenzenes are hydrogenated over Ni-Cr2O3 to give o- and p-alkoxyanilines (I). Treating I with KSCN and Br gave the corresponding II and III, resp., which were converted into the corresponding amides (IV) and (V), resp. Thus, a mixture of 0.3 mole alkoxynitrobenzene, 50 cc. EtOH, and 4 g. Ni-Cr2O3 catalyst was hydrogenated in an autoclave at 110-20°/100 atm. for 10-12 hrs., filtered, and distilled to give 74.8-86.3% I. From I the following II and III were prepared (R, m.p., m.p. hydrochloride, and % yield given): 6-Et, 159-60°, 199-200°, 60.9; 4-Et, 76-8°, 176-8°, 51.9; 6-Pr, 127-9°, 189-90°, 86.5; 6-iso-Pr, 158-9°, 191-3°, 80.2; 4-Pr, 114-15°, 160-1°, 51.2; 6-Bu, 119-21°, 140-1°, 89.6; 6-iso-Bu, 160-1°, 189-91°, 69.1. A mixture of 0.05 mole acyl chloride and 150 cc. 1:1 Me2CO-dioxane placed in a flask connected with extractor in which a paper extraction shell containing 0.1 mole II or III was placed, was heated on a water bath to complete solution of II or III, filtered, washed with Me2CO, and crystallized from EtOH to obtain the following IV (R, R1, m.p., and % yield given): Et, iso-PrCO, 91-2°, 45.5; Et, Bz, 109-10°, 80.5; Et, MeOC6H4CO (A), 120-2°, 85.3; Et, EtOC6H4CO (B), 116-18°, 76; Et, PrOC6H4CO (C), 94-7°, 84.1; Et, iso-PrOC6H4CO (D), 94-6°, 84.2; Et, BuOC6H4CO (E), 97-8°, 81; Et, PhSO2 (F), 155-7°, 87.4; Et, 2-furoyl (G), 129-30°, 83.3; Et, 2-benzofuroyl (H), 152-4°, 71.8; Et, 2-(2,3-dihydrobenzofuroyl) (I), 110-12°, 70.6; Pr, EtC6H4CO, 191-2°, 79; Pr, G, 224-5°, 80.9; Pr, I, 169-70°, 79.1; and the following V (same data): Et, PrCO, 172-3°, 53.3; Et, iso-PrCO, 140-1°, 45.4; Et, Bz, 222-5°, 87.2; Et, A, 198-200°, 86.9; Et, B, 212-13°, 70.1; Et, C, 224-6°, 84.7; Et, D, 197-200°, 73; Et, F, 199-202°, 60.1; Et, E, 202-3°, 68; Et, iso-BuOC6H4CO, 221-2°, 60; Et, G, 158-9°, 51.9; Et, H, 216-17°, 64.6; Et, I, 142-3°, 90.5; Pr, Bz, 220-2°, 69.2; Pr, A, 145-6°, 80; Pr, B, 204-6°, 86.8; Pr, C, 192-4°, 81.1; Pr, D, 189-90°, 91.8; Pr, E, 197-8°, 67.9; Pr, F, 200-2°, 85.4; Pr, G, 151-2°, 79.5; Pr, H, 212-13°, 65.3; Pr, I, 120-1°, 73.4; iso-Pr, iso-PrCO, 136-9°, 40.3; iso-Pr, BuCO, 138-40°, 49; iso-Pr, Bz, 225-6°, 83.7; iso-Pr, A, 228-9°, 73.1; iso-Pr, B, 215-16°, 60; iso-Pr, F, 255-6°, 68.8; iso-Pr, G, 181-4°, 58.6; Bu, BuCO, 140-1°, 70.6; Bu, Bz, 184-6°, 84.6; Bu, A, 181-2°, 50.1; Bu, B, 182-4°, 81.1; Bu, E, 195-7°, 69.8; Bu, H, 158-60°, 76.5; iso-Bu, A, 222-3°, 85.1; Et, ClCH2CO, 170-1°, 81.4; Bu, ClCH2CO, 172-3°, 70.4. A mixture of 0.03 mole Et2NH, 25 cc. EtOH, 0.01 mole (N-6-alkoxy-2-benzothiazolyl)-2-chloroacetamide, and 25 cc. EtOH was heated on a water bath 2-3 hrs., EtOH was distilled, the residue alkalized with 10% NaHCO3 and extracted with Et2O, the extract dried with Na2SO4 and distilled to give the corresponding V: (R, R1, b.p./mm., m.p., and % yield given): Et, Et2NCH2CO, 218-20°/5, 90-2°, 31.9; Bu, Et2NCH2CO, 130-3°/5, 121-2°, 48.3. This study involved multiple reactions and reactants, such as 6-Butoxybenzo[d]thiazol-2-amine (cas: 14372-65-7Name: 6-Butoxybenzo[d]thiazol-2-amine).

6-Butoxybenzo[d]thiazol-2-amine (cas: 14372-65-7) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, π-excessive heteroaromatic containing one sulfur atom and one pyridine-type nitrogen atom at position 3 of the cyclic ring system.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Name: 6-Butoxybenzo[d]thiazol-2-amine

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

New heterocyclic modifiers of oxidative drug metabolism. I. 6-Substituted-2-aminobenzothiazoles was written by Murray, Michael;Lacey, Ernest;Farrell, Geoffrey C.. And the article was included in Biochemical Pharmacology in 1986.COA of Formula: C10H12N2OS The following contents are mentioned in the article:

A series of 6-substituted-2-aminobenzothiazoles(2-AB) I (R = H, alkoxy, halo, etc.) was synthesized and evaluated as in vitro inhibitors of microsomal mixed-function oxidase  [9038-14-6] activity (as aminopyrine N-demethylase  [9037-69-8]) from phenobarbitone-induced rat liver. Using physiochem. parameters and multiple regression anal., QSAR was derived in which 82% of the data variance was accounted for in terms of the hydrophobic character of the inhibitor and the molar refractivity of the 2-AB 6-substituent. In contrast, literature equations derived from earlier studies with heterocyclic systems possessing nonpolar substituents underestimated by up to an order of magnitude the potency of the present compounds Kinetic studies revealed the 6-n-propoxy-2-AB, one of the more potent compounds, was a pure competitive inhibitor of aminopyrine N-demethylase activity (K_i = 60 μM from Dixon anal.), suggesting the the binding of substrate and inhibitor is mutually exclusive at the cytochrome P 450  [9035-51-2] active site. Binding studies indicated that most 2-AB derivatives elicited mixed-type I-reverse type I optical difference spectra in phenobarbitone-induced microsomes. The overlap of these components resulted in nonlinear double reciprocal plots of the spectral titrations and precluded the determination of binding parameters. In contrast, the more potent inhibitors (the 6-propoxy and 6-butoxy derivatives of 2-AB) were type I ligands with quite high affinity for ferric cytochrome P 450. Although no quant. relationship was apparent between inhibition and spectral binding affinity, a good correlation was observed between inhibition potency (I₅₀) and the capacity of 10 2-AB derivatives to prevent substrate (aminoipyrine) binding to cytochrome P 450. These findings suggest that 2-AB derivatives may inhibit microsomal oxidation via a direct competitive effect on substrate binding to cytochrome P 450. The present study also demonstrates that substitution of heterocyclic systems with hydrophilic groups does not necessarily produce weak inhibitors of mixed-function oxidase activity, and that extrapolation of existing QSAR equations to new inhibitor series must be interpreted with caution. This study involved multiple reactions and reactants, such as 6-Isopropoxybenzo[d]thiazol-2-amine (cas: 15850-81-4COA of Formula: C10H12N2OS).

6-Isopropoxybenzo[d]thiazol-2-amine (cas: 15850-81-4) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). There are numerous natural products that possess a thiazole ring with broad pharmacological activities. Thiamine, also known as vitamin B1, possesses a thiazole ring linked with 2-methylpyrimidine-4-amine as hydrochloride salt.COA of Formula: C10H12N2OS

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

New heterocyclic modifiers of oxidative drug metabolism. I. 6-Substituted-2-aminobenzothiazoles was written by Murray, Michael;Lacey, Ernest;Farrell, Geoffrey C.. And the article was included in Biochemical Pharmacology in 1986.Computed Properties of C11H14N2OS The following contents are mentioned in the article:

A series of 6-substituted-2-aminobenzothiazoles(2-AB) I (R = H, alkoxy, halo, etc.) was synthesized and evaluated as in vitro inhibitors of microsomal mixed-function oxidase  [9038-14-6] activity (as aminopyrine N-demethylase  [9037-69-8]) from phenobarbitone-induced rat liver. Using physiochem. parameters and multiple regression anal., QSAR was derived in which 82% of the data variance was accounted for in terms of the hydrophobic character of the inhibitor and the molar refractivity of the 2-AB 6-substituent. In contrast, literature equations derived from earlier studies with heterocyclic systems possessing nonpolar substituents underestimated by up to an order of magnitude the potency of the present compounds Kinetic studies revealed the 6-n-propoxy-2-AB, one of the more potent compounds, was a pure competitive inhibitor of aminopyrine N-demethylase activity (K_i = 60 μM from Dixon anal.), suggesting the the binding of substrate and inhibitor is mutually exclusive at the cytochrome P 450  [9035-51-2] active site. Binding studies indicated that most 2-AB derivatives elicited mixed-type I-reverse type I optical difference spectra in phenobarbitone-induced microsomes. The overlap of these components resulted in nonlinear double reciprocal plots of the spectral titrations and precluded the determination of binding parameters. In contrast, the more potent inhibitors (the 6-propoxy and 6-butoxy derivatives of 2-AB) were type I ligands with quite high affinity for ferric cytochrome P 450. Although no quant. relationship was apparent between inhibition and spectral binding affinity, a good correlation was observed between inhibition potency (I₅₀) and the capacity of 10 2-AB derivatives to prevent substrate (aminoipyrine) binding to cytochrome P 450. These findings suggest that 2-AB derivatives may inhibit microsomal oxidation via a direct competitive effect on substrate binding to cytochrome P 450. The present study also demonstrates that substitution of heterocyclic systems with hydrophilic groups does not necessarily produce weak inhibitors of mixed-function oxidase activity, and that extrapolation of existing QSAR equations to new inhibitor series must be interpreted with caution. This study involved multiple reactions and reactants, such as 6-Butoxybenzo[d]thiazol-2-amine (cas: 14372-65-7Computed Properties of C11H14N2OS).

6-Butoxybenzo[d]thiazol-2-amine (cas: 14372-65-7) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. The nitrogen in thiazole is sp2 hybridized and the lone pair of electrons localized on the nitrogen is less reactive due to increased aromatic character and decreased basicity. It is protonated and alkylated/acylated at nitrogen forming hydrochloride and quaternary thiazolium salt.Computed Properties of C11H14N2OS

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica