Category: 22876-19-3

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.

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.

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

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

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

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

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.

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).

22876-19-3 5-Chlorobenzo[d]oxazole-2(3H)-thione 708870, abenzoxazole compound, is more and more widely used in various.

Reference£º
Patent; SANDOZ AG; BARTH, Roland; KAUFMANN, Marius; (97 pag.)WO2016/20404; (2016); 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-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 ¡Á 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 synthetic route of 22876-19-3 has been constantly updated, and we look forward to future research findings.

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

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.

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¡Á100 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]+.

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

Reference£º
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

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.

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.

22876-19-3 5-Chlorobenzo[d]oxazole-2(3H)-thione 708870, abenzoxazole compound, is more and more widely used in various.

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

Step 2 2.97 g (15.9 mmol) of the compound obtained in Step 1 and 4.43 g (23.8 mmol) of 1-tert-butyloxycarbonylpiperazine were placed in a 250 mL flask, /j-xylene was added thereto, and the mixtue was incubated at 138 C for 15 hrs. The reaction mixture was concentrated under a reduced pressure, dissolved in ethylacetate, and washed with water. The formed organic layer was washed with a sodium hydrogen carbonate solution and a saturated NaCl solution, dried over anhydrous magnesium sulfate, filtered, and distilled under a reduced pressure. The resulting residue was subjected to silica gel column chromatography (n-hexane: ethyl acetate = 9:1) to obtain te/t-butyl 4-(5-chlorobenzooxazol-2-yl)pirhoerazine-l-carboxylate (yield: 63%).

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

Reference£º
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; CHEMON INC.; WO2008/153325; (2008); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem