Category: 30536-19-7

Qi, Mei-Ling published the artcileValidated liquid chromatography method for assay of tizanidine in drug substance and formulated products, Quality Control of 30536-19-7, the publication is Analytica Chimica Acta (2003), 478(2), 171-177, database is CAplus.

A new isocratic stability indicating HPLC method for determination of tizanidine in drug substance and formulated products is described. Chromatog. separation of tizanidine from the related substances and degraded products was achieved with a Hypersil CN column (150 mm×5.0 mm, 5 μm) using a mobile phase comprising a mixture of an ion-pairing solution of heptanesulfonic acid sodium salt (HAS), methanol and acetonitrile (50:57:18 (volume/volume)) within 10 min. The flow-rate was 1.0 mL/min and detection was made at 227 nm. The method has good selectivity towards tizanidine, related substances and degraded products. Limits of quantitation for tizanidine and its synthetic intermediates were determined, ranging from 0.051 to 0.54 μg/mL. The linearity range was found to be 2-20 μg/mL (r=0.9998, n=5). Mean recovery for tizanidine from the tablets was from 99.5 to 99.8%. Precision of the method was 1.0% (n=9). The method can be used for routine anal. and the quality control of tizanidine drug substance and its formulated products.

Analytica Chimica Acta published new progress about 30536-19-7. 30536-19-7 belongs to thiazole, auxiliary class Other Aromatic Heterocyclic,Chloride,Amine, name is 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine, and the molecular formula is C6H4ClN3S, Quality Control of 30536-19-7.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Wu, Bei published the artcileImproved synthesis of tizanidine hydrochloride, Category: thiazole, the publication is Zhongguo Xinyao Zazhi (2006), 15(8), 621-623, database is CAplus.

The synthetic way of tizanidine hydrochloride [i.e., 5-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-2,1,3-benzothiadiazol-4-amine hydrochloride] is reported. Tizanidine hydrochloride was synthesized using 4-chloro-2-nitroaniline as a starting material via several steps, including reduction with hydrazine/Fe-C, cyclization, nitration and reduction of nitro group with Fe/HOAc, condensation of 5-chloro-4-amino-2,1,3-benzothiadiazole with N-acetyl-2-imidazolidinone, alcoholysis and salt formation. The total yield of the target compound was 52.4%. The structure of the target compound was confirmed by IR, ¹H-NMR, ¹³C-NMR, MS and element anal. This improved synthetic procedure was mild and easily manipulated.

Zhongguo Xinyao Zazhi published new progress about 30536-19-7. 30536-19-7 belongs to thiazole, auxiliary class Other Aromatic Heterocyclic,Chloride,Amine, name is 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine, and the molecular formula is C2H4ClNO, Category: thiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Xu, Jia published the artcileSynthesis of tizanidine hydrochloride, Product Details of C6H4ClN3S, the publication is Zhongguo Yiyao Gongye Zazhi (2005), 36(10), 593-595, database is CAplus.

Tizanidine hydrochloride [i.e., 5-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-2,1,3-benzothiadiazol-4-amine hydrochloride] was synthesized from 4-chloro-2-nitroaniline by reduction with Zn/NaOH, cyclization, nitration and reduction of nitro group with Fe/HOAc to afford 5-chloro-4-amino-2,1,3-benzothiadiazole which subsequently was subjected to condensation with 1-acetyl-2-imidazolidinone, hydrolysis and then HCl salt formation with an overall yield of 46%.

Zhongguo Yiyao Gongye Zazhi published new progress about 30536-19-7. 30536-19-7 belongs to thiazole, auxiliary class Other Aromatic Heterocyclic,Chloride,Amine, name is 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine, and the molecular formula is C10H15NO, Product Details of C6H4ClN3S.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Nazare, Marc published the artcileA flexible, palladium-catalyzed indole and azaindole synthesis by direct annulation of chloroanilines and chloroaminopyridines with ketones, Name: 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine, the publication is Angewandte Chemie, International Edition (2004), 43(34), 4526-4528, database is CAplus and MEDLINE.

The “ringmaster” [Pd(tBu₃P)₂] served as the catalyst in the direct synthesis of indoles, e.g., I, by annulation of ortho-chloroanilines with ketones. This versatile method can be used to synthesize a variety of functionalized indoles and azaindoles, e.g., II.

Angewandte Chemie, International Edition published new progress about 30536-19-7. 30536-19-7 belongs to thiazole, auxiliary class Other Aromatic Heterocyclic,Chloride,Amine, name is 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine, and the molecular formula is C6H4ClN3S, Name: 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Samei, Amit published the artcileSimultaneous estimation of related impurities of tizanidine hydrochloride in its active pharmaceutical ingredient by reversed-phase liquid chromatography, Recommanded Product: 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine, the publication is Asian Journal of Chemistry (2009), 21(1), 176-182, database is CAplus.

A simple method was developed for qual. and quant. estimation of tizanidine hydrochloride and its 5 structurally related impurities using a reversed-phase liquid chromatog. This method was validated as per ICH guidelines for ‘validation for anal. procedures’ Q2B. The liquid chromatog. was set up in UV detection mode at 310 nm. A separation was achieved between tizanidine and all 5 impurities in a gradient programming using YMC Pack Pro C₁₈ (250 mm × 4.6 mm), 5 μ column at 1 mL/min flow rate. This method was established to be linear in a concentration range of (0.5-4.0 μg/mL) for all the components considered in this study. Limit of detection (LOD) and limit of quantification (LOQ) values were found to be (0.1-0.15 μg/mL) and (0.3-0.45 μg/mL) for tizanidine hydrochloride and its 5 related impurities, resp. Recoveries of all spiked impurities in tizanidine hydrochloride were in a range of (95-105%). Robustness and sample solution stability studies demonstrated the ruggedness of this method. This method is simple, sensitive and provides precisely accurate results.

Asian Journal of Chemistry published new progress about 30536-19-7. 30536-19-7 belongs to thiazole, auxiliary class Other Aromatic Heterocyclic,Chloride,Amine, name is 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine, and the molecular formula is C6H4ClN3S, Recommanded Product: 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

D’yachenko, E. K. published the artcileFormamidines. Benzo-2,1,3-thia(selena)diazoles, Computed Properties of 30536-19-7, the publication is Zhurnal Organicheskoi Khimii (1987), 23(11), 2450-4, database is CAplus.

The title formamidines I (R¹ = H, R² = H, Me; R¹ = Cl, R² = H, Cl; R¹ = Me, R² = H, Cl; R¹ = R² = Br) were prepared in 40-86% yields by Vilsmeier reaction of the corresponding amines with POCl₃-DMF in benzene or by reaction with HCO₂H in the presence of hexametapol. Addnl. obtained were 78-87% formamidines II (R³ = H, Me, Cl) and 72% selenium derivative III. All compounds possessed acaricidal activity but were less active than halekron.

Zhurnal Organicheskoi Khimii published new progress about 30536-19-7. 30536-19-7 belongs to thiazole, auxiliary class Other Aromatic Heterocyclic,Chloride,Amine, name is 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine, and the molecular formula is C6H4ClN3S, Computed Properties of 30536-19-7.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Quan, Zheshan published the artcileSynthesis of 4-amino-5-chloro-2,1,3-benzothiadiazole, Safety of 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine, the publication is Huaxue Shiji (2003), 25(2), 115, 117, database is CAplus.

4-Amino-5-chloro-2,1,3-benzothiadiazole was synthesized in 61.2% overall yield from 4-chloro-2-nitro-aniline as raw material by reduction, cyclization, nitration and reduction The structure of the product obtained was confirmed by MS and ¹HNMR.

Huaxue Shiji published new progress about 30536-19-7. 30536-19-7 belongs to thiazole, auxiliary class Other Aromatic Heterocyclic,Chloride,Amine, name is 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine, and the molecular formula is C6H4ClN3S, Safety of 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Reddy, Ghanta Mahesh published the artcileIdentification and characterization of potential impurities of tizanidine hydrochloride, Application of 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine, the publication is Analytical Chemistry: An Indian Journal (2008), 7(8), 586-590, database is CAplus.

During the anal. of laboratory batches of Tizanidine HCl, six impurities were detected by a simple isocratic reverse-phase high performance liquid chromatog. (HPLC) whose area percentage ranged from 0.10 to 0.30%. A through study has been undertaken to isolate and characterize these impurities, LCMS was performed to identify the mass number of the impurities. The structures of the impurities characterized as: N-(4,5-dihydro-1H-imidazol-2-yl)-2,1,3-benzothiadiazole-4-amine hydrochloride [imp A], N-(5-chloro-2,1,3-benzothiadiazol-4-yl)thiourea (imp B), dimer of Tizanidine HCl (imp C), S-methyl-N-(5-chloro-2,1,3-benzothiadiazol-4-yl)-isothiouronium iodide (imp D), 4-amino-5-chloro-2,1,3-benzothiadiazole (imp E), and N,N-bis(5-chloro-2,1,3-benzothiadiazol-4-yl)-N-(4,5-dihydro-1H-imidazol-2-yl)guanidine (imp F).

Analytical Chemistry: An Indian Journal published new progress about 30536-19-7. 30536-19-7 belongs to thiazole, auxiliary class Other Aromatic Heterocyclic,Chloride,Amine, name is 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine, and the molecular formula is C6H4ClN3S, Application of 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Korobkov, V. S. published the artcileElectronic spectra of 2,1,3-benzothiadiazole and its derivatives, Recommanded Product: 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine, the publication is Spektroskopiya, Metody i Primenenie, Akad. Nauk SSSR, Sibirsk. Otd. (1964), 130-1, database is CAplus.

The ultraviolet absorption spectra, 2110-4400 A., were obtained for 2,1,3-benzothiadiazole, 4,7-dibromo-, 4-amino-5-chloro-, 4-amino-5-bromo-, 4-amino-5,7-dichloro-, 4-amino-5,7-dibromo-, and tetrabromotetrahydro-2,1,3-benzothiazole, 3′,4′-dichlorohydro-1,2-naphth-1,2,3-thiadiazole, and 4′-chloro-1′,2′-naphth-2,1,3-thiadiazole. In general, the typical spectra of condensed aromatic rings were found.

Spektroskopiya, Metody i Primenenie, Akad. Nauk SSSR, Sibirsk. Otd. published new progress about 30536-19-7. 30536-19-7 belongs to thiazole, auxiliary class Other Aromatic Heterocyclic,Chloride,Amine, name is 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine, and the molecular formula is C6H4ClN3S, Recommanded Product: 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Pesin, V. G. published the artcileChemistry of 2,1,3-thiadiazole. V. Nitration of some mono- and dihalo derivatives of benzo-2,1,3-thiadiazole, Recommanded Product: 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine, the publication is Zhurnal Obshchei Khimii (1957), 2599-604, database is CAplus.

cf. C.A. 52, 3790i. Nitration of 2.5 g. 6-chlorobenzo-2,1,3-thiadiazole in 10 ml. concentrated H₂SO₄ at 0° with 1 ml. concentrated HNO₃ and 3 ml. H₂SO₄, finally 45 min. at 20° gave 2.9 g. 4-nitro-5-chlorobenzo-2,1,3-thiadiazole, m. 141°, which with Fe-aqueous AcOH gave a 4-amino analog (I), m. 92°. Similarly were prepared: 92% 4-nitro-5-bromobenzo-2,1,3-thiadiazole, m. 122°, and its 4-amino analog, m. 114°; also, 4-nitro-5,7-di-chlorobenzo-2,1,3-thiadiazole, m. 127-8°, and its 4-amino analog, m. 171°. Treatment of 0.93 g. I in 6 ml. 98% AcOH with 0.65 g. dichloramine with 1.5 ml. concentrated HCl and 6 ml. AcOH at 12° gave yellow 4-amino-5,7-dichlorobenzo-2,1,3-thiadiazole, m. 171°. Nitration of 4,6-dibromobenzo-2,1,3-thiadiazole as above gave 97% 7-nitro derivative, m. 155.5-56°, which reduced to the 7-amino derivative, m. 160°. Treatment of 4-amino-5-bromobenzo-2,1,3-thiadiazole with Br₂ in AcOH gave 4-amino-5,7-dibromobenzo-2,1,3-thiadiazole, m. 162-3°. To 370 g. PhNH₂ in 370 ml. MePh was added at 50-60° 400 ml. SOCl₂ in 400 ml. MePh, the last part being added at 100°; heating 30 hrs. gave 85% thionylaniline, b. 198-200°. To 39 g. SnCl₄ in 80 ml. concentrated HCl at 60° was added in 1 hr. 10 g. 4-bromo-2-nitroaniline, yielding after 1 hr. after treatment with NaOH 88.1% 4-bromo-1,2-diamino-benzene, which (7.5 g.) in 12 ml. MePH was treated with 12 ml. thionylaniline and heated 1 hr. on steam bath, then treated with 4% HCl, yielding 96.5% 5-bromobenzo-2,1,3-thiadiazole, m. 61°. Similar treatment of 3,5-dibromo-ο-phenylenediamine gave 98% 4,6-dibromobenzo-2,1,3-thiadiazole, m. 127-8°.

Zhurnal Obshchei Khimii published new progress about 30536-19-7. 30536-19-7 belongs to thiazole, auxiliary class Other Aromatic Heterocyclic,Chloride,Amine, name is 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine, and the molecular formula is C6H4ClN3S, Recommanded Product: 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica