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.

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].

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：
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

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.

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.

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; 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.

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%).

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 22876-19-3, 5-Chlorobenzo[d]oxazole-2(3H)-thione

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

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.

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, 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; MERCK SHARP & DOHME CORP.; Fleitz, Fred; Mangion, Ian; Yin, Jingjun; (11 pag.)US9441254; (2016); B2;,
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.

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 < 20C. DMF (4.59 g, 62.8 mmol) was added dropwise. A vigorous gas formation was observed and the suspension turned into a solution halfway throughout the addition. The reaction mixture was stirred for 20 minutes. Two additional aliquots oxalyl chloride (1 : 0.20g, 1.35 mmol; 2: 0.40 g, 2.70 mmol) were added and the reaction mixture was stirred for 1.5 hours. HPLC indicated complete conversion of 2-mercapto-5-chlorobenzoxazol into 2,5- Dichlorobenzoxazol . 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; SANDOZ AG; BARTH, Roland; HOeFERL-PRANTZ, Kathrin; RICHTER, Frank; WIDSCHWENTER, Gerhard; (166 pag.)WO2016/20405; (2016); A1;,
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.

INVENTIVE EXAMPLE 41 5-Chloro-2-(4-methyl-1-homopiperazinyl)benzoxazole 5-Chloro-2-mercaptobenzoxazole (1 g) was dissolved in toluene (50 ml), N-methylhomopiperazine (3.3 ml) was added dropwise to the solution and then the mixture was stirred with heating for 2 hours. After evaporation of the solvent, the thus obtained mixture was purified by a silica gel column chromatography (methylene chloride_methanol=20:1) to obtain the title compound 5-chloro-2-(4-methyl-1-homopiperazinyl)-benzoxazole (882 mg).

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

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.

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

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.

Thionyl Chloride (540 mL) and Dimethyl formamide (270 mL) were added to a stirred mixture of 5-Chloro-1,3-benzoxazole-2-thiol (540 g, 2.903 moles) and dichloromethane (5 liter) at 5-10 C. and stirred till clear solution was observed. The reaction mixture was then stirred at 10 C. to room temperature for 4 hour. After completion of the reaction, the mixture was poured into cold water (4 liter), neutralized with solid sodium bicarbonate (1440 g) portion wise over a period of 1 hour and extracted with dichloromethane (2*2.5 liter). The combined organic extracts were washed with brine solution, dried over anhydrous sodium sulphate (300 g) and concentrated under reduced pressure to give a crude compound. The crude material was triturated with Hexane (2*2 liter) at -20 C., filtered and and dried under reduced pressure to obtain 2,5-dichloro-1,3-benzoxazole (475 g, 88.9%) as a yellow liquid.

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; DR. REDDY’S LABORATORIES LIMTED; IQBAL, Javed; DAHANUKAR, Vilas Hareshwar; ORUGANTI, Srinivas; KANDAGATLA, Bhaskar; (23 pag.)US2016/168138; (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.

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).

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; 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.

To the suspension of 18′ (9.40 g, 50.64 mmol) in toluene (120 mL) was added cyclohexylamine (11.5 mL, 101 mmol) and refluxed for 48 h. The solvent was evaporated and residue was purified by silica gel column chromatography (gradient: hexanes to 30% ethyl acetate in hexanes) to afford 19′ (7.00 g, 74%) as a light orange solid. 1H NMR (400 MHz, CDCl3) delta 7.31 (s, IH), 7.13 (d, J = 12 Hz, IH), 6.99-6.97 (m, IH), 5.08 (bs, IH), 3.78-3.70 (m, IH), 2.14-2.1 1 (m, 2H), 1.81-1.76(m, 2H),1.65-1.57 (m, 2H), 1.49-1.31 (m, 2H), 1.29-1.28 (m, 2H); MS: ESI m/z 251 [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; RENOVIS, INC.; KAUB, Carl; GOWLUGARI, Sumithra; KINCAID, John; JOHNSON, Russell, James; O’MAHONY, Donogh, John Roger; ESTIARTE-MARTINEZ, Maria, de los Angeles; DUNCTON, Matthew; WO2010/39186; (2010); A2;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem