Category: benzoxazole

2-Benzoxazolinone, cas is 59-49-4, it is a common heterocyclic compound, the benzoxazole compound, its synthesis route is as follows.,59-49-4

General procedure: Intermediates 10-17 were prepared following literature methods [49] with slight modifications. 2-Benzoxazolone 8 or 2-benzothiazolone 9 (7.4mmol), appropriate 1-omega-dibromoalkane (8mmol), potassium carbonate (8mmol) and acetone (10mL) were refluxed for 4h and then allowed to stand at room temperature. The mixture was filtered to eliminate inorganic material and then evaporated under reduced pressure to obtain a residue, which was taken up in water. The solution was extracted with dichloromethane (3¡Á50 mL) and the combined extracts were washed with water, dried, and evaporated. The residue was triturated twice with light petroleum ether 40-60C to give intermediates 10-17 that were used without further purification in the subsequent steps. Analytical and spectral data are reported only for unknown compounds 13 and 17.

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Reference£º
Article; Salerno, Loredana; Pittala, Valeria; Modica, Maria N.; Siracusa, Maria A.; Intagliata, Sebastiano; Cagnotto, Alfredo; Salmona, Mario; Kurczab, Rafa?; Bojarski, Andrzej J.; Romeo, Giuseppe; European Journal of Medicinal Chemistry; vol. 85; (2014); p. 716 – 726;,
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5676-60-8, 2-Methylbenzo[d]oxazol-6-amine is a benzoxazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,5676-60-8

General procedure: To a solution of compound 3 (3.37 mmol) in DMF (10 mL), charged respective compound V (a-p) (4.04 mmol) and heated to 80 C. After3 h, TLC analysis showed complete conversion of starting materials. The reaction mixture was cooled to room temperature, charged water (30 mL) and extracted with EtOAc (2 ¡Á 20 mL). The combined organic layer was washed with water (20 mL) followed by brine and concentrated under reduced pressure to obtain gummy liquid. This crude material was triturated with MTBE to afford desired product as solid and which used as such in next step without any further purification.

The synthetic route of 5676-60-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Balraju, Vadla; Jogula, Sridhar; Krishna, Vagolu Siva; Meda, Nikhila; Sriram, Dharmarajan; Bioorganic Chemistry; vol. 100; (2020);,
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A common heterocyclic compound, the benzoxazole compound, name is 7-Aminobenzo[d]oxazol-2(3H)-one,cas is 81282-60-2, mainly used in chemical industry, its synthesis route is as follows.,81282-60-2

To a solution of [6-(trifluoromethyl)-3-pyridyl)]-methanamine (lg, 4.7 mmol) in THF (30 mL) was added CDI (2.1 mol eq) and the mixture was heated at 70C overnight. The reaction mixture was evaporated, water was added and the aqueous phase was extracted with EtOAc (3×20 mL). The recombined organic phases were anhydrified over Na2SO4 and evaporated at reduced pressure (quantitative yield). The oil obtained (0.34g, 1.2 mmol) was dissolved in DMF (15 mL) and the bicyclic amine lc (Scheme 3) was added (0.8 mol eq), then the mixture obtained was heated at 100C overnight. The solvent was removed at reduced pressure and the residue was purified by chromatography (1 : 1 EtOAc:petroleum ether) to obtain the product as a white solid (0.064g, 20% Yield). ‘HNMR (DMSO, 200 MHz) delta 4.46 (d, 2H, J=6), 6.66 (d, 1H, J=8), 6.96 (t, 1H), 7.04 (bt, 1H), 7.64 (d, 1H, J=8), 7.86 (m, 2H), 8.70 (s, 1H), 8.77 (s, 1H), 1 1.60 (bs, 1H). [M+1] 358.02 (Ci5HnF3N4O3 requires 357.27).

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Patent; PHARMESTE S.R.L.; NAPOLETANO, Mauro; TREVISANI, Marcello; PAVANI, Maria Giovanna; FRUTTAROLO, Francesca; WO2011/120604; (2011); A1;,
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59-49-4, 2-Benzoxazolinone is a benzoxazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Mix 1514.2kg of 99.3% pure 2-benzoxazolone (VI) with 4500 kg of methanol, add 1295.7kg of sodium iodide, 3000kg of sulfuric acid, mix, heat up to 34-38 degrees, add 960.9kg mass fraction 30% hydrogen peroxide was added dropwise, and the reaction was completed until 2841.3 kg of 6-iodo-2-benzimidazolone (VIII) having a purity of 99.2% was obtained in a yield of 97.03%., 59-49-4

59-49-4 2-Benzoxazolinone 6043, abenzoxazole compound, is more and more widely used in various fields.

Reference£º
Patent; Shao Yutian; (12 pag.)CN110156712; (2019); A;,
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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.

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

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Patent; SANDOZ AG; BARTH, Roland; KAUFMANN, Marius; (97 pag.)WO2016/20404; (2016); A1;,
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A common heterocyclic compound, the benzoxazole compound, name is 5-Nitro-2,3-dihydro-1,3-benzoxazol-2-one,cas is 3889-13-2, mainly used in chemical industry, its synthesis route is as follows.,3889-13-2

Synthesis of 5-aminobenzo[d]oxazol-2(3H)-one (39-2) (0488) The mixture of 39-1 (5.1 g, 28.31 mmol), Pd/C (0.5 g) and HCO2NH4 (8.9 g, 141.57 mmol) in MeOH (200 mL) was stirred at room temperature overnight. Filtered with kiselguhr, concentrated in vacuo, the residue was added 5% NaHCO3 solution, collected the solid and washed with water (50 mL), dried in vacuo to get compound 39-2 as a brown solid (4 g, yield 94%).

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Patent; Nivalis Therapeutics, Inc.; Wasley, Jan; Rosenthal, Gary J.; Sun, Xicheng; Strong, Sarah; Qiu, Jian; US9138427; (2015); B2;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.177492-52-3,Benzo[d]oxazol-6-amine,as a common compound, the synthetic route is as follows.

General procedure: Procedure A: The isothiocyanate compound (1 equiv) was added to the solution of amine (1 equiv) in 5 ml of a mixture of dichloromethane and acetonitrile (1:1, v/v). The mixture was cooled to 0C. Then, triethylamine (2 equiv) was added gradually. The mixture was stirred at 0C for 15 min, after which stirring was continued at room temperature for 2-10 h. The reaction mixture was concentrated, extracted with dichloromethane, and washed with brine.The organic layer was dried over MgSO4 and purified by column chromatography (MeOH/CH2Cl2) or by preparative TLC (MeOH/CH2Cl2) to afford the desired product.

177492-52-3, 177492-52-3 Benzo[d]oxazol-6-amine 584120, abenzoxazole compound, is more and more widely used in various fields.

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Article; Lee, Jeewoo; Tran, Phuong-Thao; Hoang, Van-Hai; Thorat, Shivaji A.; Kim, Sung Eun; Ann, Jihyae; Chang, Yu Jin; Nam, Dong Woo; Song, Hyundong; Mook-Jung, Inhee; Lee, Jiyoun; Bioorganic and Medicinal Chemistry; vol. 21; 13; (2013); p. 3821 – 3830;,
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72752-81-9, Methyl 2-mercaptobenzo[d]oxazole-6-carboxylate is a benzoxazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

72752-81-9, To a suspension of this pink solid (320 g, 1.53 mol) and K2CO3 (276 g, 2 mol) in EtOAc (3L) was added MeI (238.9g, 1.68 mol) below 20C. The mixture was stirred at room temperature for 12 hours. TLC (EtOAc/petroleum ether = 1:3) indicated the reaction was complete. Water (2L) was added to the mixture. The organic phase was separated, dried over Na2SO4 and concentrated to give 13 (320 g, 93.8%) as a pink solid.

The synthetic route of 72752-81-9 has been constantly updated, and we look forward to future research findings.

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Article; Jonckers, Tim H.M.; Rouan, Marie-Claude; Hache, Geerwin; Schepens, Wim; Hallenberger, Sabine; Baumeister, Judith; Sasaki, Jennifer C.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 15; (2012); p. 4998 – 5002;,
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A common heterocyclic compound, the benzoxazole compound, name is Methyl benzo[d]oxazole-7-carboxylate,cas is 1086378-35-9, mainly used in chemical industry, its synthesis route is as follows.,1086378-35-9

The compound obtained in Example 51-2 (1.221 g, 6.89 mmol) and THF (24 ml), was dissolved in ethanol (24 ml), cooled with ice. Thereto calcium chloride (1.529 g, 13.78 mmol), sodium borohydride (1.043 g, 27.56 mmol) was stirred at room temperature for 2 hours added. After the reaction was extracted with ethyl acetate by adding 1 mol / l hydrochloric acid. It was washed with a saturated aqueous sodium bicarbonate solution. Dried with magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (SNAP ULTRA 25 g, hexane / ethyl acetate) to give the title compound (149 mg, 14.5%) as a white solid.

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Patent; Yakult Honsha Co., Ltd.; University of Occupational and Environmental Health; Ono, Masahiro; Kobayashi, Tsuneyuki; Yamazaki, Ryuta; Haibara, Hirotake; Nishiyama, Yukiko; Hokkyo, Atsuko; Nishiyama, Hiroyuki; Kurita, Akinobu; Matsuzaki, Ken; Kono, Kimitoshi; Izumi, Hiroto; (215 pag.)JP2016/124812; (2016); A;,
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A common heterocyclic compound, the benzoxazole compound, name is 6-Bromobenzo[d]oxazol-2(3H)-one,cas is 19932-85-5, mainly used in chemical industry, its synthesis route is as follows.,19932-85-5

General procedure: IV, e.g. bromo-substituted 3H-1,3-benzoxazol-2-one, (1 eq.) was suspended in a 1:1 toluene/EtOH mixture (10 mL per mmol IV). The boronic acid V (1.5 eq.) was added followed by aq. NaCO3 (2 M, 0.55 mL per mmcl IV, 1.1 eq.). The resulting suspension was degassed undernitrogen for 10 mm, followed by addition of Pd(PPh3)4 (0.1 eq.) and heating under microwave irradiation at 100 C for 30 mm. The reaction mixture was diluted with EtOAc (40 mL per mmcl IV), and water (40 mL per mmcl IV) was added. The two phases were separated and the aqueous layer was extracted with EtOAc (2 x 40 mL per mmcl IV). The combined organic phases were dried over Na2SO4, evaporated on silica, and the compound was purified by column chromatography using the Teledyne ISCO apparatus (cyclohexane:EtOAc).The title compound was obtained according to the General Procedure II, starting from 6-bromobenzoxazolone (500 mg, 2.34 mmol) and (4-fluorophenyl)boronic acid (490 mg, 3.50mmol). White solid (450 mg, 42%). 1H NMR (400 MHz, CDCI,) 6 7.08 (m, 3H), 7.33 (dd, J = 8.1, 1.6 Hz, 1H), 7.39 (d, J = 1.4 Hz, 1H), 7.47 -7.52 (m, 2H), 7.91 (s, 1H). MS (ESI) m/z: 228 [M-H].

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Patent; FONDAZIONE ISTITUTO ITALIANO DI TECNOLOGIA; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; UNIVERSITA’ DEGLI STUDI DI PARMA; PIOMELLI, Daniele; PIZZIRANI, Daniela; BACH, Anders; SCARPELLI, Rita; MELZIG, Laurin; MOR, Marco; (72 pag.)WO2015/173169; (2015); A1;,
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