Category: 22876-19-3

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 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.

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

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

INVENTIVE EXAMPLE 1 5-Chloro-2-(4-methyl-1-piperazinyl)benzoxazole A 300 mg portion of 5-chloro-2-mercaptobenzoxazole was suspended in 50 ml of anhydrous benzene, and the suspension was mixed with 404 mg of phosphorus pentachloride and heated under reflux for 3 hours. The reaction solution was cooled in an ice bath and, with stirring, 1.6 g of 1-methylpiperazine was added thereto. After 30 minutes of stirring, the ice bath was removed to carry out 12 hours of stirring at room temperature, and then the reaction solution was mixed with saturated sodium bicarbonate aqueous solution and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried with magnesium sulfate and then the solvent was evaporated under a reduced pressure. Thereafter, the thus obtained mixture was purified by a silica gel column chromatography (ethyl acetate_methanol=20:1) to obtain the title compound (121 mg) in light yellow color. 1 H-NMR (CD3 OD) delta values: 2.35 (3 H, s), 2.60 (4 H, t), 3.70 (4 H, t), 7.02 (1 H, dd), 7.25 (1 H, d), 7.28 (1 H, d) MS (EI): m/z 251 (M+)

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：
Patent; Meiji Seika Kaisha, Ltd; Koichi Shudo; US6037342; (2000); A;,
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.

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, 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：
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

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.

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).

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; 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.

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. 2-[(3-Bromopropyl)thio]-5-chlorobenzo[d]oxazole (9)The title compound was obtained as pink oil (96%); 1H NMR (500 MHz, DMSO-d6): delta7.76 (d, J = 1.9Hz, 1H, benzoxazole), 7.68 (d, J = 8.5 Hz, 1H, benzoxazole), 7.36 (dd, J = 8.5, 1.9 Hz, 1H,benzoxazole), 3.66 (t, J = 6.5 Hz, 2H, CH2Br), 3.44 (t, J = 7.0 Hz 2H, SCH2), 2.37-2.32 (m, 2H,CH2CH2CH2). 13C NMR (125 MHz, DMSO-d6): delta165.99, 150.02, 142.50, 128.86, 124.14, 117.98,111.41, 32.72, 31.61, 30.26. Anal. (C10H9BrClNOS) C, H, N, S.

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：
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

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

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.

(1) Synthesis of 4beta-S-(6-chlorobenzoxazole-2)-podophyllotoxin: 414 mg (1 mmol) of podophyllotoxin,201 mg (1 mmol) of 6-chlorobenzoxazole-2-thiol, dried under vacuum for 1 h, using 15 mL of trifluoroacetic acid as solvent in ice bath.The mixture was stirred under vacuum for 1 to 3 hours, and chloroform acetone was used as a developing solvent to detect the end point of the reaction. Adding the reaction system to 20 to 50 times the volumeIn deionized water, the filter cake was collected by filtration and washed to obtain a crude product.

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：
Patent; Tang Yajie; Zhao Wei; (23 pag.)CN108285456; (2018); A;,
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.

General procedure: A mixture of intermediate compound N-(3-(1H-tetrazole-5-yl) phenyl)-2-chloroacetamideand benzo[d]oxazole-2-thiol or benzo[d]thiazole-2-thiol or 2-mercapto benzimidazoles in anequimolar amount were taken and refluxed with acetone (20 mL) in the presence of K2CO3for 24 hr. The reaction was monitored by TLC and on completion of the reaction, an excessof solvent was evaporated at room temperature and the reaction mixture was diluted withwater (about 200 mL). The diluted hydrochloric acid was added to precipitate the productwhich was further filtered and thoroughly washed with cold water.

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; Maheshwari, Neelesh; Karthikeyan, Chandrabose; Bhadada, Shraddha V.; Verma, Amit K.; Sahi, Chandan; Moorthy, N.S. Hari Narayana; Trivedi, Piyush; Bioorganic Chemistry; vol. 92; (2019);,
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.

Step 3: Preparation of 2, 5-dichloro-1 ,3-benzoxazole.5-chloro-1 ,3-benzoxazole-2-thiol (8.09 g, 43.6 mmol) dissolved in CHCI3 (65 mL) and stirred at ice bath for 10 minutes. Chlorine gas was bubbled into the solution for 10 minutes. The reaction mixture was further stirred at room temperature overnight. The reaction mixture was poured into ice water (70 mL) and extracted with aq. 2N NaOH (30mLx2), then ice water (30mL). The CHCI3 solution was allowed to stand for 10 minutes, then filtered through a plug of silica gel to give clear solution. The solvent was removed under reduced pressure to afford semi-oil crude product. The crude product was dissolved in CHCI3 (25 mL) and filtered through diatomaceous earth. The solvent was removed under reduced pressure to give the title compound as a solid.

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：
Patent; PFIZER INC.; SPRINGER, John, Robert; VAZQUEZ, Michael, Lawrence; WO2011/77313; (2011); 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.

A mixture of 5-chloro-benzooxazole-2-thiol (4.00 g, 21.5 mmol, 1.0 equiv; commercially available from Aldrich) and ethyl 4-amino-1-piperidine carboxylate (4.9 g, 28.0 mmol, 1.3 equiv) in anhydrous DMAc (5 mL) was heated to 200 C. under microwave irradiation for 20 min. To the crude reaction mixture was added a conc. solution of sodium chloride (100 mL), the solution extracted with ethyl acetate (3×100 mL) and the combined organic phases dried over MgSO4. Purification of the crude material with column chromatography on silica eluting with hexane/ethyl acetate (2:1?1:1) yielded 2.7 g (39%) of the title compound. 1H NMR (400 MHz, DMSO): delta 1.19 (t, J=7.1 Hz, 3H), 1.39-1.45 (m, 2H), 1.93-1.97 (m, 2H), 2.98 (br s, 2H), 3.77-3.78 (m, 1H), 3.91-3.95 (m, 2H), 4.04 (q, J=7.1 Hz, 2H), 7.00 (dd, J=8.4 Hz, J=2.1 Hz, 1H), 7.29 (d, J=2.1 Hz, 1H), 7.36 (d, J=8.4 Hz, 1H), 8.19 (d, J=7.6 Hz, 1H). 13C NMR (100 MHz, DMSO): delta 14.53, 31.11, 42.07, 49.60, 60.63, 109.45, 115.10, 119.65, 127.78, 144.86, 146.71, 154.56, 162.50. MS (ISP): 324.1 [M+H]+.

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; Binggeli, Alfred; Christ, Andreas Dominik; Green, Luke Gideon Granville; Guba, Wolfgang; Maerki, Hans-Peter; Martin, Rainer Eugen; Mohr, Peter; US2006/205718; (2006); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem