Category: benzoxazole

As a common heterocyclic compound, it belongs to benzoxazole compound, name is Methyl benzo[d]oxazole-4-carboxylate, and cas is 128156-54-7, its synthesis route is as follows.

General procedure: To a degassed solution (N2 was purged for 10 min) of methyl 1,3-benzoxazole-4-carboxylate (150 mg, 0.847mmol) and N-(2-iodophenyl)benzamide 2a (273 mg, 0.847 mmol) in anhydrous toluene (4ml) , CuI (32 mg, 0.169 mmol), xantphos (98 mg, 0.169 mmol), Pd(OAc)2 (10 mg, 0.042 mmol), Cs2CO3 (685 mg, 2.117 mmol) were added at room temperature under nitrogen atmosphere. Reaction mixture was continued for 20 hours at reflux condition. After the completetion of the reaction (monitored by TLC), Reaction mixture was filtered through celite bed and washed with methanol (10 ml),filtrate was concentrated. Crude mass which was purified by column chromatography over silica gel (230-400 mesh) using DCM-Methanol (1:9) as elutant to affordthe products 3a (284 mg) as white solid. All the other compounds 3b-3r were prepared similarly following the above procedure.

128156-54-7, 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.,128156-54-7 ,Methyl benzo[d]oxazole-4-carboxylate, other downstream synthetic routes, hurry up and to see

Reference：
Article; Sasmal, Swarnendu; Sen, Indira; Hall, Roger G.; Pal, Sitaram; Tetrahedron Letters; vol. 56; 11; (2015); p. 1374 – 1377;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

90322-32-0, 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. 2-Methylbenzo[d]oxazole-5-carboxylic acid, cas is 90322-32-0,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

Step 2 – Preparation of Intermediate H 5-Carboxy-2-methylbenzoxazole (8.9 g) and methyl- p -toluenesulfonate (11.16 g) were combined and heated to 200C with stirring for 10 minutes. The mixture became a brown liquid and mild boiling occured. The reaction was cooled to room temperature and the liquid solidified. Acetone (50 ml) was added, and with constant heating at reflux, the product was broken up with a spatula. The resulting slurry was heated at reflux for 15 minutes with rapid stirring and the off-white product was collected by filtration. This product was slurried again in refluxing acetone for 30 minutes, filtered, washed with ligroin P950, and dried to yield 9.3 g of 5-carboxy-2,3-dimethylbenzoxazolium p -toluenesulfonate (Intermediate H).

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 2-Methylbenzo[d]oxazole-5-carboxylic acid, 90322-32-0

Reference：
Patent; EASTMAN KODAK COMPANY, (a New Jersey corporation); EP294461; (1991); B1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

701-16-6, 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-Fluoro-2-methylbenzo[d]oxazole, cas is 701-16-6,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

[0614] To a stirred solution of Comp-50c (0.073 g, 0.48 mmol) in mixture of THF (5 mL) and tBuOH (0.5 mL) was added t-BuOK (0.16 g, 1.46 mmol) at 0 C. Comp-80b (0.1 g, 0.48 mmol) was added portion wise and the reaction mixture was stirred at RT for 16 h. Progress of the reaction was monitored by TLC and LCMS. After completion, the reaction mixture was quenched with H20 (5 mL) and extracted with EtOAc (10 mL X 2). The organic layer was washed with brine, separated, dried over anhydrous Na2SC>4 and concentrated under reduced pressure. The crude obtained was purified by column chromatography (silica, 100- 200 mesh, 2-5% EtOAc in hexane) to afford (E)-2-(2-(l-cyclohexyl-2,5-dimethyl-lH-pyrrol- 3-yl)vinyl)-5-fluorobenzo[d]oxazole (104, 0.08 g, 51%) as a yellow solid. (1076) [0615] HPLC Purity: 99.4% (1077) [0616] MS (ESI) m/e [M+H]+/ Rt’%: 339.15/2.56/99.8% (1078) [0617] 1H NMR (400 MHz, DMSO-d6) delta 1.17 – 1.27 (m, 2 H), 1.35 – 1.45 (m, 2 H), 1.62 – 1.69 (m, 1 H), 1.73 – 1.96 (m, 6 H), 2.22 – 2.27 (m, 3 H), 2.35 – 2.39 (m, 3 H), 6.20 – 6.25 (m, 1 H), 6.46 – 6.53 (m, 1 H), 7.09 – 7.16 (m, 1 H), 7.41 – 7.48 (m, 1 H), 7.60 – 7.66 (m, 1 H), 7.66 – 7.70 (m, 1 H).

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-Fluoro-2-methylbenzo[d]oxazole, 701-16-6

Reference：
Patent; ALPINE ANDROSCIENCES, INC.; PATIL, Santhosh N.; SARMA, Bugga VNBS; (148 pag.)WO2019/152731; (2019); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belongs to benzoxazole compound, name is 2-Benzoxazolinone, and cas is 59-49-4, its synthesis route is as follows.

NaH (280 mg, 7.00 mmol) was added to a chilled (0 0C) solution of benzo[d]oxazol-2(3H)- one (650 mg, 4.81 mmol) in tetrahydrofuran (20 mL). After 0.5 hours, methyl iodide (1.03 g, 7.25 mmol) was added dropwise with stirring, maintaining a temperature of 0 0C. The resulting solution was then stirred for 6 hours at room temperature. The reaction mixture was then quenched by the addition of ethanol (10 mL), and the mixture was concentrated. Water (50 mL) was then added and the resulting solution was extracted with dichloromethane (3 x 20 mL). The organic layers were combined, dried (Na2SO4), filtered and concentrated to afford 0.62 g (82%) of 3-methylbenzo [d] oxazol-2 (3H)-one as a light red solid.

59-49-4, 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.,59-49-4 ,2-Benzoxazolinone, other downstream synthetic routes, hurry up and to see

Reference：
Patent; MEMORY PHARMACEUTICALS CORPORATION; WO2007/98418; (2007); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belongs to benzoxazole compound, name is 6-Bromobenzo[d]oxazol-2(3H)-one, and cas is 19932-85-5, its synthesis route is as follows.

Intermediate 13: 2-oxo-2,3-dihydrobenzo[d]oxazole-6-carbonitrile To a solution of 6-bromo benzoxazolinone (2 g, 9.4 mmol) in DMF (20 mL) was added CuCN (16.79 g, 188 mmol), and the reaction was stirred at 175 C. for 6 h. The reaction progress was monitored by TLC (100% EtOAc). The reaction was diluted with EtOAc (10 mL) and filtered through Celite brand filter agent. The organic layer was concentrated and purified by column chromatography (silica gel, 0-50% EtOAc in hexanes) to give the title compound. MS (ESI pos. ion) m/z: 158.9 (MH-).

19932-85-5, 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.,19932-85-5 ,6-Bromobenzo[d]oxazol-2(3H)-one, other downstream synthetic routes, hurry up and to see

Reference：
Patent; AMGEN INC.; BISWAS, Kaustav; CHEN, Jian J.; GORE, Vijay Keshav; HARRIED, Scott; HORNE, Daniel B.; KALLER, Matthew R.; MA, Vu Van; SHAM, Kelvin; ZHONG, Wenge; US2014/45855; (2014); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

81282-60-2, 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. 7-Aminobenzo[d]oxazol-2(3H)-one, cas is 81282-60-2,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of 14.9 g N-methyldiethanolamine (3), 44.5 g triethylamine and 120 ml methyl ethyl ketone (MEK) a mixture of 51.6 g methanesulfonic anhydride and 100 ml MEK was dosed at 0 C. Subsequently 14.5 g methanesulfonic acid was dosed at 0 C. After which, 14.5 g 7-amino-2(3H)-benzoxazolone (2) was added and the mixture was heated to reflux followed by a reflux period of 48 hours during which the product crystallized. The product was filtered off after cooling to 0 C. and washed with MEK. The product was dried at 50 C. and 100 mbar to constant weight. The overall yield of this step was about 67% (crude on crude).

The chemical industry reduces the impact on the environment during synthesis,81282-60-2,7-Aminobenzo[d]oxazol-2(3H)-one,I believe this compound will play a more active role in future production and life.

Reference：
Patent; Rheenen, Jeroen Van; Muijselaar, Wilhelmus G.H.M.; Teunissen, Hendrik; US2011/86862; (2011); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belongs to benzoxazole compound, name is 6-Bromobenzo[d]oxazol-2(3H)-one, and cas is 19932-85-5, its synthesis route is as follows.

Step 2: Bromide 1 (12.8 g, 59.6 mmol) was dissolved in anhydrous THF (220 mL), and the solution was cooled to ?78 C. Solutions of MeMgBr (21.9 mL of a 3.0 M solution in Et2O, 65.6 mmol), sec-BuLi (50.4 mL of a 1.3 M solution in cyclohexane, 65.6 mmol), and 1,4-Cyclohexanedione mono-ethylene ketal (11.2 g, 71.5 mmol) in anhydrous THF (10 mL) were added sequentially at 30-minute intervals. After the final addition, the reaction mixture was allowed to warm to room temperature. The reaction was quenched by the addition of 1N HCl (25 mL). The reaction mixture was diluted with EtOAc (500 mL), washed with saturated NaCl (250 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to provide a mixture of 2 and 3, as a brown oil.

19932-85-5, 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.,19932-85-5 ,6-Bromobenzo[d]oxazol-2(3H)-one, other downstream synthetic routes, hurry up and to see

Reference：
Patent; Nikam, Sham Shridhar; Scott, Ian Leslie; Sherer, Brian Alan; Wise, Lawrence David; US2003/236252; (2003); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

It is a common heterocyclic compound, the benzoxazole compound, 2-Methylbenzo[d]oxazol-6-amine, cas is 5676-60-8 its synthesis route is as follows.

A slurry of 4-amino-2-methylquinoline (0.158 g) in dichloromethane (10 ml) was added to solution of carbonyl diimidazole (0.162 g) in dichloromethane (5 ml). The mixture was stirred for 2.5 h, solvent removed at reduced pressure and the residue dissolved in dimethylformamide (15 ml). 6-Amino-2-methylbenzoxazole (0.148 g) (Res. Inst. Drugs, Modra, Slovakia. Collect. Czech. Chem. Commun. (1996), 61, 371-380) was added and the mixture warmed to 100 C. for 1 h. Solvent was removed at reduced pressure and triturated with diethyl ether and methanol to give the title compound (0.035 g) as a colourless solid. 1 H NMR delta: 2.59 (3H, s), 2.60 (3H, s), 7.24 (1H, dd, J=1.9, 8.5 Hz), 7.58-7.63 (2H, m), 7.73 (1H, t, J=7.2 Hz),7.89 (1H, d, J=7.7 Hz), 8.06 (1H, d, J=1.8 Hz), 8.13-8.15 (2H, m), 9.22 (1H, brs), 9.55 (1H, brs). m/z (API+): 333 (MH+).

5676-60-8, 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.,5676-60-8 ,2-Methylbenzo[d]oxazol-6-amine, other downstream synthetic routes, hurry up and to see

Reference：
Patent; SmithKline Beecham p.l.c.; US6699879; (2004); B1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belongs to benzoxazole compound, name is 6-Bromo-2-methylbenzo[d]oxazole, and cas is 151230-42-1, its synthesis route is as follows.

j00660j To a solution of 6-bromo-2-methylbenzo[djoxazole (0.12 g, 0.55 mmol), compound (R)A-2 (0.10 g, 0.55 mmol), tris(dibenzylideneacetone)dipalladium(0) (51 mg, 0.05 5 mmol) and 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene (64 mg, 0.11 mmol) in dioxane (2 mL) under nitrogen at room temperature was added cesium carbonate (0.36 g, 1.1 mmol). The reaction mixture was stirred at 100 C for 2 hours, then filtered and concentrated in vacuo. The residue was purified by prepHPLC [Instrument: GX-A; Column: Phenomenex Gemini C18 250×50 mm, particle size: 10 tm; Mobile phase: 23-53% acetonitrile in H20 (add 0.05% NH3 H20, v/v)j and lyophilized to give:Compound (R)-51 (27 mg, 16% yield) as a yellow solid: cSFC analytical (R) tR=6.239 mm., purity: 97.35%; LCMS (GG): tRl.664 mm., (ES) m/z (M+H)=3 13.2; ?H-NMR(CD3OD, 400 MHz): 7.89 (d, J=1.6 Hz, 1H), 7.45 (d, J=8.8 Hz, 1H), 7.16 (dd, J18.4 Hz, J22.0 Hz, 1H), 3.34 (s, 1H), 3.16-3.06 (m, 3H), 2.91-2.76 (m, 4H), 2.59 (s, 3H), 2.19-2. 14 (m, 1H), 2.04 (s, 1H), 1.79-1.70 (m, 2H), 1.57-1.53 (m, 1H).

151230-42-1, 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.,151230-42-1 ,6-Bromo-2-methylbenzo[d]oxazole, other downstream synthetic routes, hurry up and to see

Reference：
Patent; FORUM PHARMACEUTICALS, INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; McRINER, Andrew, J.; (267 pag.)WO2017/69980; (2017); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belongs to benzoxazole compound, name is 6-Nitrobenzo[d]oxazole, and cas is 17200-30-5, its synthesis route is as follows.

General procedure: A mixture of VNU-11(Hf) (0.018 g, 0.01 mmol), aromatic acylchloride (0.140 g, 1 mmol) and benzoxazole (0.119 g, 1 mmol)was heated at 170 C under conventional heating for a few hoursor microwave irradiation of a CEM Discover apparatus for a fewminutes. After completion of reaction, the catalyst was filteredfrom the reaction mixture. The filtrate was diluted with ethyl acetate (50 mL), washed with H2O (3×20 mL), aqueous NaHCO3(2 x20 mL), and dried over Na2SO4. The solvent was removed ina rotary evaporator. The crude product was purified by flash chromatography(90:10 acetone/petroleum ether to give correspondingproduct. The purity and identity of the products were confirmed byGC-MS spectra, which were compared with the spectra in the NISTlibrary, and by 1H and 13C NMR spectroscopy.

17200-30-5, 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.,17200-30-5 ,6-Nitrobenzo[d]oxazole, other downstream synthetic routes, hurry up and to see

Reference：
Article; Nguyen, Linh Ho Thuy; Nguyen, Trang Thi Thu; Tran, Phuong Hoang; Kawazoe, Yoshiyuki; Le, Hung Minh; Doan, Tan Le Hoang; Journal of Catalysis; vol. 374; (2019); p. 110 – 117;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem