Category: 939-69-5

939-69-5, 6-Hydroxybenzo[d]thiazole-2-carbonitrile is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

939-69-5, Method A: Preparation of a 5-Oxymethyl-D-Luciferin Cycloheximide Conjugate [00190] 5-Hydroxymethyl-D-Luciferin. A modification of the procedure of Seto, S., et al., 1963 is used. A mixture of 2-Cyano-6-hydroxybenzthiazole (200 mg), ?-hydroxymethyl D-Cysteine (200 mg), potassium carbonate (160 mg) and 50% aqueous methanol (10 mL) is stirred under a stream of nitrogen gas, at room temperature for 2.5 hours. After neutralization with 1 N aqueous HCl, the precipitate is collected, washed with water and recrystallized from 95% ethanol to give the title compound. [00191] 6′-O-t-butyldimethylsilyl-5-hydroxymethyl-D-Luciferin, t-butyldimethylsilyl ester. Under anhydrous conditions. 5-hydroxymethyl-D-Luciferin (45mg, 0.145 mmole) is dissolved in anhydrous dimethylformamide (7 mL), cooled to 0 C. (ice-bath) and imidazole (300 muL) and t-butyldimethylsilyl chloride solution (50% solution in tetrahydrofuran, 52 muL, 2.1 equiv.) is added. The reaction mixture is allowed to stir at 0 C. for 2 hours and at room temperature overnight. The major product is purified by silicagel column chromatography using dichloromethane:ethylacetate gradient elution. Fractions containing the first major product to elute from the column are combined and evaporated to give the title compound as a white solid.

939-69-5 6-Hydroxybenzo[d]thiazole-2-carbonitrile 9881912, athiazole compound, is more and more widely used in various fields.

Reference：
Patent; Marker Gene Technologies, Inc.; US6656917; (2003); B1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

939-69-5, 6-Hydroxybenzo[d]thiazole-2-carbonitrile is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

939-69-5, To the solution of benzene sulfonyl chloride derivative (0.7 g, 2.98 mmol) and 2-cyano-6-hydroxoylbenzothiazole or 2-cyano-6-hydroxyquinoline (2.84 mmol) in 10 ml of dry methylene chloride, triethylamine (0.58 g, 5.68 mmol) at room temperature was added, and the resultant mixture stirred for 3 hours. The product was purified by flash chromatography using heptane/methylene chloride (1/2) as eluent. (yield 85percent): 1H NMR (CDCl3) delta(ppm): 8.30 (d, J= 2.0 Hz, 1H), 8.16 (d, J= 9.3 Hz, 1H), 8.13 (dd, J = 8.7 Hz, J= 2.0 Hz, 1H), 8.04 (d, J = 8.7 Hz, 1H), 7.78 (d, J = 2.4 Hz, 1H), 7.27 (dd, J = 9.0 Hz, J = 2.4 Hz, 1H), 2.95 (s, 3H, CH3). MS (ES) m/e (M+1): 376.

939-69-5 6-Hydroxybenzo[d]thiazole-2-carbonitrile 9881912, athiazole compound, is more and more widely used in various fields.

Reference：
Patent; Promega Corporation; HUANG, Fen; KLAUBERT, Dieter; SHULTZ, John; ZHOU, Wenhui; (54 pag.)EP2611929; (2016); B1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.939-69-5,6-Hydroxybenzo[d]thiazole-2-carbonitrile,as a common compound, the synthetic route is as follows.

939-69-5, Example 2 Synthesis of Compounds 5 and 11 2-Cyano-6-pivaloyloxybenzothiazole. A solution of 2-cyano-6-hydroxybenzothiazole (2.1 g, 12.5 mmol) in 30 mL of dry THF under inert atmosphere was treated with pyridine (2.0 g, 25 mmol) followed by pivaloyl chloride (1.95 g, 16.2 mmol). This reaction was stirred 15 h at room temperature. The reaction mixture was then diluted with 100 mL of distilled water, and this solution was extracted with ethyl acetate (4*50 mL). The combined organics were washed with aqueous sodium bicarbonate (2*100 mL) and distilled water (1*100 mL), then dried over Na2 SO4 and concentrated under reduced pressure to afford 3.0 g of a thick oil. This material was chromatographed on silica gel and 1.8 g of the product was eluted with 10percent ethyl acetate/hexanes. 1 H NMR (CDCl3): delta 1.39 (s, 9H); 7.34-7.38 (m, 1H); 7.74-7.75 (d, 1H); 8.20-8.23 (d, 1H).

939-69-5 6-Hydroxybenzo[d]thiazole-2-carbonitrile 9881912, athiazole compound, is more and more widely used in various fields.

Reference：
Patent; Lumigen, Inc.; US6045991; (2000); A;; ; Patent; Lumigen, Inc.; US5965736; (1999); A;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.939-69-5,6-Hydroxybenzo[d]thiazole-2-carbonitrile,as a common compound, the synthetic route is as follows.,939-69-5

General procedure: The hydroxy- or methoxycarbonitrile derivative (1 eq) was added to the cysteine derivative (1.05 eq) and sodium carbonate (3 eq) in 5 ml water. The mixture was stirred at room temperature for three hours before addition of dilute HCl (1 M) to pH ? 3.5 ? 4.0. The product was isolated by extraction with diethyl ether, washed by water, followed by evaporation

939-69-5 6-Hydroxybenzo[d]thiazole-2-carbonitrile 9881912, athiazole compound, is more and more widely used in various fields.

Reference：
Article; Rothweiler, Ulli; Eriksson, Jonas; Stensen, Wenche; Leeson, Frederick; Engh, Richard A.; Svendsen, John S.; European Journal of Medicinal Chemistry; vol. 94; (2015); p. 140 – 148;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

939-69-5, 6-Hydroxybenzo[d]thiazole-2-carbonitrile is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

939-69-5, The mixture of 6-hydroxy-2-cyanobenzothiozole(0.311 g, 1.77 mmol), 3-chloropropyldimethylamine hydrochloride (0.36 g, 2.27 mmol), potassium carbonate (0.63g, 4.57 mmol) and sodium iodide (0.034 g) in acetone (30 ml) was heated to reflux overnight. Upon cooling to roomtemperature, the insoluble solid was removed by filtration. The compound was purified by flash chromatography usingmethylene chloride/methanol (96:4) as eluent in a yield of 86percent (0.387 g).1H NMR (CD2Cl2): 7.98 (d, J= 9.3 Hz, 1H), 7.32 (d, J= 2.4 Hz, 1H), 7.16 (dd, J = 9.0 Hz, J= 2.1 Hz, 1H), 4.04 (t, J = 6.4Hz, 2H, OCH2), 2.36 (t, J = 7.2 Hz, 2H, NCH2), 2.13 (s, 6H, CH3), 1.90 (m, 2H, CH2).

As the paragraph descriping shows that 939-69-5 is playing an increasingly important role.

Reference：
Patent; Promega Corporation; Cali, James J.; Daily, William; Hawkins, Erika; Klaubert, Dieter; Liu, Jianquan; Meisenheimer, Poncho; Scurria, Michael; Shultz, John W.; Unch, James; Wood, Keith V.; Zhou, Wenhui; Valley, Michael P.; (202 pag.)EP2277872; (2016); B1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

939-69-5,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.939-69-5,6-Hydroxybenzo[d]thiazole-2-carbonitrile,as a common compound, the synthetic route is as follows.

General procedure: The hydroxy- or methoxycarbonitrile derivative (1 eq) was added to the cysteine derivative (1.05 eq) and sodium carbonate (3 eq) in 5 ml water. The mixture was stirred at room temperature for three hours before addition of dilute HCl (1 M) to pH ? 3.5 ? 4.0. The product was isolated by extraction with diethyl ether, washed by water, followed by evaporation

As the paragraph descriping shows that 939-69-5 is playing an increasingly important role.

Reference：
Article; Rothweiler, Ulli; Eriksson, Jonas; Stensen, Wenche; Leeson, Frederick; Engh, Richard A.; Svendsen, John S.; European Journal of Medicinal Chemistry; vol. 94; (2015); p. 140 – 148;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.939-69-5,6-Hydroxybenzo[d]thiazole-2-carbonitrile,as a common compound, the synthetic route is as follows.

To a solution of 6-hydroxy-2-cyanobenzothiozole (0.50 g, 2.84 mmol) and 2-nitrobenzene-sulfonyl chloride (0.63 g, 2.84 mmol) in 15 ml of anhydrous methylene chloride, TEA (0.58 g, 5.68 mmol) was added. The resultant mixture was stirred for 3 hours. The product was purified by flash chromatography using heptane/ethyl acetate/methylene chloride (70/30/15) as eluent in a yield of 55percent., 939-69-5

The synthetic route of 939-69-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Promega Corporation; HUANG, Fen; KLAUBERT, Dieter; SHULTZ, John; ZHOU, Wenhui; (54 pag.)EP2611929; (2016); B1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

939-69-5, 6-Hydroxybenzo[d]thiazole-2-carbonitrile is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

939-69-5, b. Synthesis of 2-cyano-6-hydroxybenzothiazole dimethyl phosphate ester. Five hundred mg (2.84 mmoles) of 2-cyano-6-hydroxybenzothiazole was placed in a 10 mL reactor vial, which could be sealed with a teflon cap and had a magnetic stir bar. A 5.0 mL aliquot of THF was added and upon stirring the 2-CBT dissolved rapidly giving a clear, light red solution. This was followed by the addition of 0.550 mL (402 mg. 3.97 mmoles) of triethylamine. The resulting clear solution was cooled to 4° C. by placing it in an ice bath. Next, 512 mg (3.54 mmoles) of dimethylchlorophosphate dissolved in 1.5 mL of THF was added to this solution over a period of 60 seconds. After approximately 20 minutes, the 10 mL reactor vial was removed from the ice bath and allowed to stir for two hours at room temperature. At this point the reaction was a thick slurry. The triethylammonium chloride salt was removed by suction filtration. The filtrate was transferred to a round-bottomed flask and concentrated on a rotoevaporator under vacuum. The residue was dissolved in 50 mL of ethyl acetate followed by the addition of 20 mL of water plus 10 mL of water saturated with NaCl. The phases were separated and the ethyl acetate layer was saved. The aqueous phase was back washed with 40 mL of ethyl acetate and this was combined with the previous ethyl acetate layer. The combined ethyl acetate solution was washed twice with a mixture of 15 mL of aqueous saturated NaCl and 5 mL of water. The ethyl acetate layer was dried over MgSO4, filtered and concentrated on a roto-evaporator at full vacuum. Approximately 5 mL of ethyl ether was added to the concentrate which dissolved the thick oil. This was cooled to -20° C. and white crystals formed rapidly. The white crystals were isolated by filtration. The melting point of the product, 2-cyano-6-hydroxybenzothiazole dimethylphosphate ester, (6-CBT-DMP) was 54.0°-55.1° C. The HPLC showed a purity of 96.4percent (by area). The column was 3.9 mm*25 mm with a flow rate of 1.0 mL/min with a linear program from 100percent water to 100percent methanol with a program time of 30 minutes. The product was monitored at 254 nm. The retention time for the product was 23.4 minutes. The NMR spectrum was determined. The solvent used for the NMR was deuterochloroform with TMS as an internal standard. There was a doublet centered at delta 3.9 with a coupling constant of 10 Hz and integrated for 6.00H’s. There was a multiplet centered at 7.9 which integrated for 3.08 hours.

As the paragraph descriping shows that 939-69-5 is playing an increasingly important role.

Reference：
Patent; JBL Scientific, Inc.; US5424440; (1995); A;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

939-69-5, 6-Hydroxybenzo[d]thiazole-2-carbonitrile is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

939-69-5, Example 4 Synthesis of Compounds 4 and 13 2-Cyano-6-t-butyldiphenylsiloxy-benzothiazole. A solution of 2-cyano-6-hydroxybenzothiazole (5.0 g, 28 mmol) in 100 ml of anhydrous DMF under inert atmosphere was treated with 2.9 g of imidazole (4.2 mmol) followed by t-butyldiphenylchlorosilane (9.34 g, 34 mmol). The reaction was stirred at room temperature for 3 h and then diluted with 200 ml of ethyl acetate and washed with water (4*400 ml). The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography, eluding with 5-10percent ethyl acetate/hexanes to afford 13.0 g of the desired product containing ~10percent silyl impurity in quantitative yield. The product was taken on without further purification. 1 H NMR (CDCl3): delta 1.12 (s, 9H); 7.13-7.46 (m, 8H); 7.70-7.72 (m, 4H); 7.92-7.95 (d, 1H).

The synthetic route of 939-69-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Lumigen, Inc.; US6045991; (2000); A;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.939-69-5,6-Hydroxybenzo[d]thiazole-2-carbonitrile,as a common compound, the synthetic route is as follows.

D-2-(6′-Hydroxybenzothiazol-2′-yl)-D2-5-(2,6-dibromo-4-cyanophenoxy)methylthiazoline-4-carboxylic acid.. A solution of 2-cyano-6-hydroxybenzthiazole (2.0 eq.) in MeOH is purged with nitrogen for 5 minutes.. A solution of (2R,3S)-2-amino-4-(2,4-dibromo4-cyanophenyl)oxy-3-mercaptobutanoic acid trifluoroacetate (1.0 eq.) and potassium carbonate (1.0 eq.) in deoxygenated water is added to the methanol solution.. The reaction is stirred under nitrogen while being protected from light for 2 hours.. The volume of the reaction is doubled with water and the resulting solution is made acidic with dilute hydrochloric acid.. The mixture is extracted with ethyl acetate.. The extract is washed with water and dried over sodium sulfate.. The solvent is removed and the residue is triturated with ether.. The residue is dried in vacuo to yield the title compound., 939-69-5

The synthetic route of 939-69-5 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Marker Gene Technologies, Inc.; US6656917; (2003); B1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica