Category: 22876-19-3

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

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.

22876-19-3, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,22876-19-3 ,5-Chlorobenzo[d]oxazole-2(3H)-thione, other downstream synthetic routes, hurry up and to see

Reference：
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, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 5-Chlorobenzo[d]oxazole-2(3H)-thione, cas is 22876-19-3,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

Example 103-[1-(5-chloro-1,3-benzoxazol-2-yl)pyrrolidin-3-yl]-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile (One Enantiomer Isolated) To a solution of 5-chloro-1,3-benzoxazole-2-thiol (0.50 g, 2.7 mmol, Aldrich) in toluene (10 mL) was added thionyl chloride (0.59 mL, 8.1 mmol) followed by a drop of DMF. The reaction was heated to reflux for 30 min and the solvent removed in vacuo. A portion of this crude product (17 mg) and 3-pyrrolidin-3-yl-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile (20.0 mg, 0.0457 mmol; enantiomer 2 from Example 9, Step 2b) were dissolved in 1,4-dioxane (0.40 mL) and N,N-diisopropylethylamine (16 microL, 0.091 mmol) was added. The mixture was heated to 70 C. for 1.5 h. The solvent was removed in vacuo and the residue was sequentially stirred with 50% TFA/DCM for 1.5 h, concentrated, then stirred with 0.3 mL EDA in methanol for 30 min. Purification via preparative-HPLC/MS (C18 column eluting with a gradient of ACN/H2O containing 0.15% NH4OH) afforded product. 1H NMR (400 MHz, d6-DMSO): delta 12.13 (br s, 1H), 8.88 (s, 1H), 8.68 (s, 1H), 8.43 (s, 1H), 7.60 (d, 1H), 7.41 (d, 1H), 7.31 (d, 1H), 7.02-6.97 (m, 2H), 4.86 (dt, 1H), 3.86 (dd, 1H), 3.68-3.59 (m, 1H), 3.54-3.28 (m, 4H), 3.03-2.90 (m, 1H), 1.77-1.67 (m, 2H); LCMS (M+H)+: 459.0, 461.0.

The chemical industry reduces the impact on the environment during synthesis,22876-19-3,5-Chlorobenzo[d]oxazole-2(3H)-thione,I believe this compound will play a more active role in future production and life.

Reference：
Patent; Rodgers, James D.; Shepard, Stacey; Arvanitis, Argyrios G.; Wang, Haisheng; Storace, Louis; Folmer, Beverly; Shao, Lixin; Zhu, Wenyu; Glenn, Joseph; US2010/298334; (2010); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

22876-19-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 5-Chlorobenzo[d]oxazole-2(3H)-thione, cas is 22876-19-3,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

Step 4b. A mixture of compound from step 4a (1.6 g, 8.6 mmol), Mel (1.8 g, 12.9 mmol) and K2CO3 in DMF (20 mL) was stirred for 5 hours at 50C before was partitioned (EtO Ac-brine). The organic was dried (Na2S04), filtered and concentrated to give the desired compound (1.2 g, 70%) as a yellow oil. ESI-MS m/z =199.90, 201.90 [M+H]+. This material was used directly in the next step without further purification.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 5-Chlorobenzo[d]oxazole-2(3H)-thione, 22876-19-3

Reference：
Patent; ENANTA PHARMACEUTICALS, INC.; QIU, Yao-ling; LI, Wei; CAO, Hui; JIN, Meizhong; GAO, Xuri; PENG, Xiaowen; KASS, Jorden; OR, Yat, Sun; (84 pag.)WO2016/183266; (2016); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

22876-19-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 5-Chlorobenzo[d]oxazole-2(3H)-thione, cas is 22876-19-3,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

Thionyl chloride (885 g, 7.5 mol)And N, N-dimethylformamide (270 ml) were added to a solution of 5-chloro-2-mercaptobenzoxazole (540 g, 2.903 mol) in dichloromethane (5 L) at 5-10 C.Stirred until a clear solution was formed and the reaction solution was stirred at room temperature for 4 hours.After completion of the reaction, the reaction solution was poured into 4 L of ice water, neutralized to neutral with sodium bicarbonate in 1 hour, and extracted with dichloromethane (2.5 L * 2).The organic layer was washed with brine, dried over sodium sulfate and dried to give the crude product. The crude product was washed with n-hexane (2 L * 2) at -20 C, filtered and dried to give yellow liquid 2,5-dichlorobenzo (496.8 g, 91.0%).

The chemical industry reduces the impact on the environment during synthesis,22876-19-3,5-Chlorobenzo[d]oxazole-2(3H)-thione,I believe this compound will play a more active role in future production and life.

Reference：
Patent; Shanghai ZaiQi Bio-Tech Co., Ltd.; Wang, Zhiguo; Song, Yanhong; Ma, Xiujuan; Tian, Beibei; Li, Shijiang; Li, Chao; Li, Qiang; Li, Tao; (8 pag.)CN106478537; (2017); A;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

22876-19-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 5-Chlorobenzo[d]oxazole-2(3H)-thione, cas is 22876-19-3,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

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).

The chemical industry reduces the impact on the environment during synthesis,22876-19-3,5-Chlorobenzo[d]oxazole-2(3H)-thione,I believe this compound will play a more active role in future production and life.

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

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

General procedure: Commercially available 5-chloro-2-mercapto benzoxazole or benzothiazole (10 mmol) and K2CO3 (15mmol) were added to 50 mL of acetone. After 10 min, appropriate 1-bromo–bromoalkane (12 mmol) was added and the mixture was stirred at room temperature for 24 h. After this time the suspension was filtered from inorganic material and the solvent was evaporated under reduced pressure. The residue was suspended in water and extracted with diethyl ether (3 × 50 mL). The combined extracts were washed with water, dried over anhydrous Na2SO4, and evaporated under reduced pressure to givein termediates 9-12 that were used without further purification for the final step. For analytical purpose,a little amount was purified by means of flash chromatography, using cyclohexane/ethyl acetate 9.5:0.5v/v as eluent. Analytical and spectral data are reported for novel compounds 9-12

22876-19-3, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,22876-19-3 ,5-Chlorobenzo[d]oxazole-2(3H)-thione, other downstream synthetic routes, hurry up and to see

Reference：
Article; Romeo, Giuseppe; Prezzavento, Orazio; Intagliata, Sebastiano; Pittala, Valeria; Modica, Maria N.; Marrazzo, Agostino; Turnaturi, Rita; Parenti, Carmela; Chiechio, Santina; Arena, Emanuela; Campisi, Agata; Sposito, Giovanni; Salerno, Loredana; European Journal of Medicinal Chemistry; vol. 174; (2019); p. 226 – 235;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

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

(iv) 47.0 g 5-chlorobenzo[d]oxazole-2-thiol were dissolved in 1300 mL CH2CI2 and 175 mL dimethylformamide at room temperature and stirring was continued until a clear solution was obtained. 26.3 mL Oxalyl chloride in 25 mL CH2CI2 was added over a period of 20 minutes (gas formation). The resulting 2,5-dichlorobenzo[22876-19-3, In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles.,22876-19-3 ,5-Chlorobenzo[d]oxazole-2(3H)-thione, other downstream synthetic routes, hurry up and to see

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

22876-19-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 5-Chlorobenzo[d]oxazole-2(3H)-thione, cas is 22876-19-3,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

2-mercapto-5-chlorobenzoxazole (100 g, 0.54 mol) and 1200 ml of dichloromethane were added to a 3 L four-necked reaction flask, Stir, Oxalyl chloride (102.6 g, 0.81 mol) was added, After adding DMF 395 ml, Room temperature reaction for 30 minutes, Triethylamine (192 g, 1.89 mol) with 1- (tert-butyl carbamate)Ethylenediamine (103.7 g, 0.65 mol), Room temperature reaction for 1 hour. Add water 1200ml, Separate the organic layer, Dried under reduced pressure to obtain a solid-liquid mixture, Purification with acetonitrile / water gave a yellow solid 110 g, yield 65.5%

The chemical industry reduces the impact on the environment during synthesis,22876-19-3,5-Chlorobenzo[d]oxazole-2(3H)-thione,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; Tianjin Pharmaceutical Institute Co., Ltd.; Kang Jiangpeng; Pan Yi; Chen Wei; Su Mujun; Fang Simeng; Tao Yong; (7 pag.)CN106632121; (2017); A;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

22876-19-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 5-Chlorobenzo[d]oxazole-2(3H)-thione, cas is 22876-19-3,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

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. The chemical industry reduces the impact on the environment during synthesis,22876-19-3,5-Chlorobenzo[d]oxazole-2(3H)-thione,I believe this compound will play a more active role in future production and life. 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

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

General procedure: Commercially available 5-chloro benzoxazoles or benzothiazoles(5 mmol) and K2CO3 (15 mmol) were added to 50 mL of DMF.The mixture was heated at 60 C and 1-(2-chloroethyl)hexahydro-1H-azepine hydrochloride (6.5 mmol) was added. The mixture was maintained at 60 C under stirring for 3 h, then was cooled to room temperature, poured into water, and extracted with diethyl ether(3 50 mL). The organic layer was washed with brine, dried overan hydrous Na2SO4 and evaporated under reduced pressure to give are sidue, which was purified by flash column chromatography oversilica gel using ethyl acetate/methanol 8:2 v/v as eluent. Immediately after solvent evaporation, free bases were converted into hydrochlorides by dissolving the corresponding amine in diethyl ether and treating with a 1.25MHCl ethanol solution (pH 1e2). The precipitate was filtered off, washed with diethyl ether, and dried under nitrogen. The following compounds were obtained using this procedure:, 22876-19-3

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

Reference£º
Article; Romeo, Giuseppe; Prezzavento, Orazio; Intagliata, Sebastiano; Pittala, Valeria; Modica, Maria N.; Marrazzo, Agostino; Turnaturi, Rita; Parenti, Carmela; Chiechio, Santina; Arena, Emanuela; Campisi, Agata; Sposito, Giovanni; Salerno, Loredana; European Journal of Medicinal Chemistry; vol. 174; (2019); p. 226 – 235;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem