Category: 22876-19-3

5-Chlorobenzo[d]oxazole-2(3H)-thione, cas is 22876-19-3, it is a common heterocyclic compound, the benzoxazole compound, its synthesis route is as follows.,22876-19-3

General procedure: A mixture of 1-(chloroacetyl)-3-(2-thienyl)-5-(1,3-benzodioxol-5-yl)-2-pyrazoline (0.005 mol) and aryl thiol (0.005 mol) in acetone (30 mL) was stirred at room temperature for 8 h in the presence of potassium carbonate (0.005 mol). The solvent was evaporated. The residue was washed with water and dried. The product was recrystallized from ethanol [18, 25].

As the rapid development of chemical substances, we look forward to future research findings about 22876-19-3

Reference£º
Article; Oezdemir, Ahmet; Sever, Belgin; Alt?ntop, Mehlika Dilek; Letters in drug design and discovery; vol. 16; 1; (2018); p. 82 – 92;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

5-Chlorobenzo[d]oxazole-2(3H)-thione, cas is 22876-19-3, it is a common heterocyclic compound, the benzoxazole compound, its synthesis route is as follows.,22876-19-3

Thiol 9a (10.5 kg, 54.6 mol) was added to a vessel and suspended in DCM (141 kg), Oxalyl chloride (10.4 kg, 82.3 mol) was added (slightly endothermic) followed by DMF (40.0 kg, 547 mol) over 1.25 h, such that the batch temperature was < 25 C. The batch was aged at 20 C for approximately 30 min, HPLC analysis showed reaction to be complete. The batch was cooled to 10 C then triethyiamine (16.64 kg, 164.4 mol) was added via a sub-surface sample line at such a rate as to maintain a batch temperature of < 10 C. A sub-surface addition protocol was required to prevent build up of triethyiamine hydrochloride solid on the walls of the vessel. The batch was cooled to 0 C, then a solution of N-Boc-ethylenediamine (10.5 kg, 61.2 mol) in DCM (10 kg) was added such that the batch temperature was < 10 C. The reaction was warmed to 20 C and stirred for 2.5 h, HPLC analysis showed the reaction to be complete. Water (63,6 kg) was charged to the batch and the mixture stirred for 5 min. The layers were separated and the aqueous phase re-extracted with DCM (42.2 kg). The organic solutions were then combined and approximately half of the total DCM volume was distilled from the batch under vacuum whilst maintaining a temperature of < 40 C. MeCN (83.3 kg) was then added and the remaining DCM removed by distillation (0.5 mol % DCM left by .H NMR wrt MeCN). MV (4.61 kg, 65,8 mol) was added to the batch followed by DBU (4.17 kg, 27.4 mol) such that the temperature was < 20 C. The batch was aged for 10 h at 20 C then analyzed by HPLC. The reaction was then diluted with water (42.4 kg) and aged for a further 30 min. The mixture was filtered and the slurry washed with MeCN (33.3 kg). The solid was washed with MeCN (~10 L) then dried in a vacuum oven (T - 60 C) for 22 h. MVK adduct 10 (15.5 kg) was isolated as an off-white solid, mp 145-148 C. NMR (400 MHz, CDC13): delta 7.24 (d, 1 H, J = 2.3 Hz), 7.09 (d, 1 H, J - 8.5 Hz), 6.91 (dd, 1 H, J = 8.5, 2.3 Hz), 5.06 (s, 1 H, br), 3.73 (t, 2 H, J = 6.7 Hz), 3.63 (t, 2 H, J = 6.1 Hz), 3.37 (d, 2 H, br), 2.89 (t, 2 H, J = 6.7 Hz), 2.14 (s, 3H), 1.33 (s, 9 H). I3C NMR (100.6 MHz, CDC13): 6 206.7, 163.0, 156.0, 147.4, 144.6, 129,2, 120,3, 1 16.6, 109.2, 79.4, 49.3, 44.3, 41.9, 39.1, 30.2, 28.3. HRMS (ESI): m/z [M+ + H] calcd for CI8H24C1N304: 382.1534; found: 382.1544. 22876-19-3 is used more and more widely, we look forward to future research findings about 5-Chlorobenzo[d]oxazole-2(3H)-thione Reference£º
Patent; MERCK SHARP & DOHME CORP.; MERCK SHARP & DOHME LIMITED; BAXTER, Carl, A.; CLEATOR, Edward; KRSKA, Shane, W.; SHEEN, Faye; STEWART, Gavin; STROTMAN, Neil; WALLACE, Debra, J.; WRIGHT, Timothy; WO2012/148553; (2012); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.22876-19-3,5-Chlorobenzo[d]oxazole-2(3H)-thione,as a common compound, the synthetic route is as follows.

Step 6) Synthesis of 2, 5-dichlorobenzo [d] oxazoleA mixture of 5-chlorobenzo [d] oxazole-2-thiol (3.01 g, 16.22 mmol) , sulfoxide chloride (20 mL, 272.6 mmol) and N, N-dimethylformamide (0.10 mL, 1.3 mmol) was heated to reflux and stirred for 3 hours The reaction mixture was cooled and the solvent was removed in vacuo. The resulting product was used directly in the next step., 22876-19-3

The synthetic route of 22876-19-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; JIN, Chuanfei; ZHANG, Ji; (90 pag.)WO2017/88759; (2017); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.22876-19-3,5-Chlorobenzo[d]oxazole-2(3H)-thione,as a common compound, the synthetic route is as follows.

Subsequently, 5-chloro-2-mercaptobenzoxazole (3.1 g, 16.7 mmol) was dissolved in thionyl chloride (30 mL, 413 mmol). DMF (1.5 mL) was added and the reaction mixture was heated at 65 C. for 45 min. The solvent was removed under reduced pressure and to the residue was added toluene (2*60 mL) followed by evaporation each time to remove the excess SOCl2 (azetrope). The resultant crude product was dissolved in ethyl acetate (100 mL), washed with water (100 mL) and dried over Na2SO4. Evaporation of ethyl acetate gave 2,5-dichlorobenzoxazole, compound 19, as a red oil (3.2 g)., 22876-19-3

As the paragraph descriping shows that 22876-19-3 is playing an increasingly important role.

Reference£º
Patent; GALLEON PHARMACEUTICALS, INC.; US2011/224269; (2011); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO334,mainly used in chemical industry, its synthesis route is as follows.,22876-19-3

Oxalyl chloride (1.20 g, 9.4 mmol) was added dropwise to a stirred suspension of 2- mercapto-5-chlorobenzoxazol (1.28 g, 6.9 mmol) in CH2C12(37 mL) at The solution of 2,5-Dichlorobenzoxazol was added to a solution of (7-Methyl-l ,4- diazepan-l-yl)(5-methyl-2-(2H-l ,2,3-triazol-2-yl)phenyl)methanone (1.88 g, 6.3 mmol) and NEt3(3.18 g, 6.3 mmol) in DMF (24 mL) at room temperature. The reaction mixture was then stirred at 70 C for 19 hours and at 90 C for 20 hours. The reaction mixture was then cooled to room temperature and quenched with a saturated solution of NaHC03(50 mL). The organic phase was separated and washed with H20 (50 mL) followed by brine (50 mL). The organic phase was dried over MgS04, filtered and concentrated to give crude Suvorexant (3.58 g).

With the synthetic route has been constantly updated, we look forward to future research findings about 5-Chlorobenzo[d]oxazole-2(3H)-thione,belong benzoxazole compound

Reference£º
Patent; SANDOZ AG; BARTH, Roland; KAUFMANN, Marius; (97 pag.)WO2016/20404; (2016); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belong benzoxazole compound,5-Chlorobenzo[d]oxazole-2(3H)-thione,22876-19-3,Molecular formula: C7H4ClNOS,mainly used in chemical industry, its synthesis route is as follows.,22876-19-3

General procedure: Phosphorus tribromide (89 muL, 0.11 mmol) was dropwisely added to a solution of commercial 2-phenethylbenzylalcohol (75 mg, 0.35 mmol) in dry THF (5 mL) at 0 C. After stirring at room temperature for 2h, the reaction mixture was extracted with EtOAc after quenching with water. The organic extract was washed with brine and dried over MgSO4. Evaporation of the filtrate provided crude 2-phenethylbenzyl bromide. Then, commercial 2-mercaptoimidazole (70 mg, 0.47 mmol), sodium hydride (22 mg, 0.55 mmol) and potassium iodide (78 mg, 0.47 mmol) was added to a solution of crude 2-phenethylbenzyl bromide in DMF (3 mL). After stirring at 100C overnight, the reaction mixture was quenched with water, extracted with EtOAc, washed with brine and dried over MgSO4 and evaporated. Purification of the residue by column chromatography on silica gel (hexane/EtOAc = 1/1) provided the title compound (44 mg, 0.15 mmol) as a colorless solid in 43% yield.

With the synthetic route has been constantly updated, we look forward to future research findings about 5-Chlorobenzo[d]oxazole-2(3H)-thione,belong benzoxazole compound

Reference£º
Article; Fukuda, Miwa; Sasaki, Tomomi; Hashimoto, Tomoko; Miyachi, Hiroyuki; Waki, Minoru; Asai, Akira; Takikawa, Osamu; Ohno, Osamu; Matsuno, Kenji; Bioorganic and Medicinal Chemistry Letters; vol. 28; 17; (2018); p. 2846 – 2849;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.22876-19-3,5-Chlorobenzo[d]oxazole-2(3H)-thione,as a common compound, the synthetic route is as follows.

Thiol 9a (10.5 kg, 54.6 mol) was added to a vessel and suspended in DCM (141 kg). Oxalyl chloride (10.4 kg, 82.3 mol) was added (slightly endothermic) followed by DMF (40.0 kg, 547 mol) over 1.25 h, such that the batch temperature was 25 C. The batch was aged at 20 C. forapproximately 30 mi HPLC analysis showed reaction to becomplete. The batch was cooled to 10 C. then triethylamine (16.64 kg, 164.4 mol) was added via a sub-surface sampleline at such a rate as to maintain a batch temperature of 10C. A sub-surface addition protocol was required to preventbuild up of triethylamine hydrochloride solid on the walls ofthe vessel. The batch was cooled to 00 C., then a solution ofN-l3oc-ethylenediamine (10.5 kg, 61.2 mol)inDCM(lOkg)was added such that the batch temperature was 10 C. Thereaction was warmed to 20 C. and stirred for 2.5 h, HPLCanalysis showed the reaction to be complete. Water (63.6 kg)was charged to the batch and the mixture stirred for 5 mm.The layers were separated and the aqueous phase re-extracted with DCM (42.2 kg). The organic solutions werethen combined and approximately half of the total DCMvolume was distilled from the batch under vacuum whilstmaintaining a temperature of 40 C. MeCN (83.3 kg) wasthen added and the remaining DCM removed by distillation(0.5 mol % DCM left by ?H NMR wrt MeCN). MVK (4.61kg, 65.8 mol) was added to the batch followed by DI3U (4.17kg, 27.4 mol) such that the temperature was 20 C. Thebatch was aged for 10 h at 20 C. then analyzed by HPLC.The reaction was then diluted with water (42.4 kg) and agedfor a further 30 mm. The mixture was filtered and the slurrywashed with MeCN (33.3 kg). The solid was washed withMeCN (.-10 L) then dried in a vacuum oven (T=60 C.) for22 h. MVK adduct 10 (15.5 kg) was isolated as an off-whitesolid. mp 145-148 C. ?H NMR (400 MHz, CDC13): oe 7.24(d, 1H, J=2.3 Hz), 7.09 (d, 1H, J=8.5 Hz), 6.91 (dd, 1H,J=8.5, 2.3 Hz), 5.06 (s, 1H, br), 3.73 (t, 2H, J=6.7 Hz), 3.63(t, 2H, J=6.1 Hz), 3.37 (d, 2H, br), 2.89 (t, 2H, J=6.7 Hz),2.14 (s, 3H), 1.33 (s, 9H). ?3C NMR (100.6 MHz, CDC13):206.7, 163.0, 156.0, 147.4, 144.6, 129.2, 120.3, 116.6,109.2, 79.4, 49.3, 44.3, 41.9, 39.1, 30.2, 28.3. HRMS (ESI):mlz [M+H] calcd for C,8H24C1N304: 382.1534; found:, 22876-19-3

The synthetic route of 22876-19-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; Fleitz, Fred; Mangion, Ian; Yin, Jingjun; (11 pag.)US9441254; (2016); B2;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.22876-19-3,5-Chlorobenzo[d]oxazole-2(3H)-thione,as a common compound, the synthetic route is as follows.

22876-19-3, General procedure: The substituted 2-aminophenol (1eq.) in water and 95% ethanol was added potassium carbonate (1eq.) and CS2 (1eq.).The mixture was heated under reflux for 3 hours. After cooling, the solution was neutralized with 15 mL of acetic acid in 30 mL water. The precipitate was collected to give 2-thiolbenzoxazoles. Then, the substituted 2-thiolbenzoxazoles (1eq.) dissolved in toluene, PCl5 (1.5eq) was added dropwise. The mixture was heated to reflux for 2 hours. After the solvent was evaporated, the crude product was purified by silica gel column chromatography using PE-EA as an eluent.

The synthetic route of 22876-19-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Ouyang, Liang; Huang, Yuhui; Zhao, Yuwei; He, Gu; Xie, Yongmei; Liu, Jie; He, Jun; Liu, Bo; Wei, Yuquan; Bioorganic and Medicinal Chemistry Letters; vol. 22; 9; (2012); p. 3044 – 3049;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

22876-19-3, 5-Chlorobenzo[d]oxazole-2(3H)-thione is a benzoxazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Thiol 9a (10.5 kg, 54.6 mol) was added to a vessel and suspended in DCM (141 kg), Oxalyl chloride (10.4 kg, 82.3 mol) was added (slightly endothermic) followed by DMF (40.0 kg, 547 mol) over 1.25 h, such that the batch temperature was < 25 C. The batch was aged at 20 C for approximately 30 min, HPLC analysis showed reaction to be complete. The batch was cooled to 10 C then triethyiamine (16.64 kg, 164.4 mol) was added via a sub-surface sample line at such a rate as to maintain a batch temperature of < 10 C. A sub-surface addition protocol was required to prevent build up of triethyiamine hydrochloride solid on the walls of the vessel. The batch was cooled to 0 C, then a solution of N-Boc-ethylenediamine (10.5 kg, 61.2 mol) in DCM (10 kg) was added such that the batch temperature was < 10 C. The reaction was warmed to 20 C and stirred for 2.5 h, HPLC analysis showed the reaction to be complete. Water (63,6 kg) was charged to the batch and the mixture stirred for 5 min. The layers were separated and the aqueous phase re-extracted with DCM (42.2 kg). The organic solutions were then combined and approximately half of the total DCM volume was distilled from the batch under vacuum whilst maintaining a temperature of < 40 C. MeCN (83.3 kg) was then added and the remaining DCM removed by distillation (0.5 mol % DCM left by .H NMR wrt MeCN). MV (4.61 kg, 65,8 mol) was added to the batch followed by DBU (4.17 kg, 27.4 mol) such that the temperature was < 20 C. The batch was aged for 10 h at 20 C then analyzed by HPLC. The reaction was then diluted with water (42.4 kg) and aged for a further 30 min. The mixture was filtered and the slurry washed with MeCN (33.3 kg). The solid was washed with MeCN (~10 L) then dried in a vacuum oven (T - 60 C) for 22 h. MVK adduct 10 (15.5 kg) was isolated as an off-white solid, mp 145-148 C. NMR (400 MHz, CDC13): delta 7.24 (d, 1 H, J = 2.3 Hz), 7.09 (d, 1 H, J - 8.5 Hz), 6.91 (dd, 1 H, J = 8.5, 2.3 Hz), 5.06 (s, 1 H, br), 3.73 (t, 2 H, J = 6.7 Hz), 3.63 (t, 2 H, J = 6.1 Hz), 3.37 (d, 2 H, br), 2.89 (t, 2 H, J = 6.7 Hz), 2.14 (s, 3H), 1.33 (s, 9 H). I3C NMR (100.6 MHz, CDC13): 6 206.7, 163.0, 156.0, 147.4, 144.6, 129,2, 120,3, 1 16.6, 109.2, 79.4, 49.3, 44.3, 41.9, 39.1, 30.2, 28.3. HRMS (ESI): m/z [M+ + H] calcd for CI8H24C1N304: 382.1534; found: 382.1544., 22876-19-3

As the paragraph descriping shows that 22876-19-3 is playing an increasingly important role.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; MERCK SHARP & DOHME LIMITED; BAXTER, Carl, A.; CLEATOR, Edward; KRSKA, Shane, W.; SHEEN, Faye; STEWART, Gavin; STROTMAN, Neil; WALLACE, Debra, J.; WRIGHT, Timothy; WO2012/148553; (2012); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.22876-19-3,5-Chlorobenzo[d]oxazole-2(3H)-thione,as a common compound, the synthetic route is as follows.

To a suspension of 5-chloro-2-mercaptobezoxazole (5.0 g, 26.9 mmol) in POCl3 (12.6 mL, 135 mmol) was added PCl5 (6.2 g, 129.6 mmol) and about 20 mL CH2Cl2. After stirring 5 days, the solvents were removed by rotary evaporation, the residue was partitioned between EtOAc and saturated aqueous NaHCO3. The layers were separated, the organic was washed with brine, dried over Na2SO4, and concentrated. The residue was dissolved in a minimum amount of CHCl3, hexanes were added, and a small amount of solids were filtered off. The filtrate was concentrated to provide D-1 as a white solid. Data for D-1: LC/MS: rt=2.38 min; m/z (M+H)=188.0 found; 188.0 required., 22876-19-3

The synthetic route of 22876-19-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Bergman, Jeffrey M.; Breslin, Michael J.; Coleman, Paul J.; Cox, Christopher D.; Mercer, Swati P.; Roecker, Anthony J.; US2008/132490; (2008); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem