Category: benzoxazole

Name is 4-Aminobenzo[d]oxazol-2(3H)-one, as a common heterocyclic compound, it belongs to benzoxazole compound, and cas is 81900-93-8, its synthesis route is as follows.

Amine 2b (289 mg, 1.2 mmol) (Scheme 7) was dissolved in 20ml of AcOEt and at 0C triphosgene (356 mg, 1.2 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound lb (180 mg, 1.2 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave lOOmg of a white solid. Yield = 20% ‘HNMR (DMSO, 200 MHz) delta 1.94 (4H, m), 3.23 (4H, m), 4.67 (2H, d, J = 5.6 Hz), 6.55 (2H, dd, J = 8.8 Hz, J’ = 1.2 Hz), 7.05 (1H, t, J = 8.2 Hz), 7.17 (2H, d, J = 7.2 Hz), 7.46 (1H, d), 9.98 (1H, t), 1 1.53 (1H, bs), 1 1.80 (1H, bs); [M+1] 421.2 (C2oH19F3N4O3 requires 420.39).

81900-93-8, 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.,81900-93-8 ,4-Aminobenzo[d]oxazol-2(3H)-one, other downstream synthetic routes, hurry up and to see

Reference：
Patent; PHARMESTE S.R.L.; NAPOLETANO, Mauro; TREVISANI, Marcello; PAVANI, Maria Giovanna; FRUTTAROLO, Francesca; WO2011/120604; (2011); A1;,
Benzoxazole – Wikipedia
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It is a common heterocyclic compound, the benzoxazole compound, Benzo[d]oxazol-2-amine, cas is 4570-41-6 its synthesis route is as follows.

[000213] To a stirred solution of crude acid chloride (70 mg, crude) in CH2C12 (5 mL) under argon atmosphere were added 2-chloro-4-fluoroaniline 184 (25 mg, 0.17 mmol) and pyridine (0.07 mL, 0.86 mmol) at 0 °C; warmed to RT and stirred for 16 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was diluted with water (20 mL) and extracted with CH2C12 (2 x 30 mL). The combined organic extracts were washed with 1 N HC1 (20 mL), 10percent NaHCO3 solution (30 mL), brine (15 mL) dried over sodium sulfate, filtered and concentrated in vacuo to obtain crude. The precipitated material was either directly dried in vacuo or triturated or purified through silica gel column chromatography /preparative HPLC or by acid-base treatment to afford the desired compound.

4570-41-6, 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.,4570-41-6 ,Benzo[d]oxazol-2-amine, other downstream synthetic routes, hurry up and to see

Reference：
Patent; INDIANA UNIVERSITY RESEARCH AND TECHNOLOGY CORPORATION; ASSEMBLY BIOSCIENCES, INC.; TURNER, William W.; ARNOLD, Lee Daniel; MAAG, Hans; ZLOTNICK, Adam; WO2015/138895; (2015); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belongs to benzoxazole compound, name is Benzo[d]oxazol-2-amine, and cas is 4570-41-6, its synthesis route is as follows.

Example I (0279) (0280) I (0281) 2-Bromopyridine (1 ) (1.0g, 6.3mmol), benzo[d]oxazol-2-amine (2) (0.871 g, 6.4mmol), Xantphos (0.37g, 0.63mmol) and Cs2C03 (3.09g, 9.4mmol) were combined in dry 1 ,4-dioxane (15mL). The reaction mixture was degassed with N2(g) and placed under vacuum for 10min. Pd2(dba)3 (0.289g, 0.31 mmol) was then added and the resulting reaction mixture was heated at 90°C for 30h. It was then poured onto demineralised water (200ml_) and extracted with EtOAc (3 x 100ml_). The organic phases were combined, dried over Na2S04, filtered and subsequently concentrated in vacuo. The resulting residue was purified by flash chromatography with EtOAc/Hexane (1 : 1) to provide N-(pyridin-2-yl)benzo[d]oxazol-2-amine (3) as a yellow solid (0.8g, 60percent). (0282) LCMS (ES): Found 212.1 [M+H]+.

4570-41-6, 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.,4570-41-6 ,Benzo[d]oxazol-2-amine, other downstream synthetic routes, hurry up and to see

Reference：
Patent; KARUS THERAPEUTICS LTD; SHUTTLEWORTH, Stephen Joseph; WHALE, Andrew David; COLMAN, Lucy Mary; ROGERS, Helen Louise; (117 pag.)WO2017/208032; (2017); 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

59-49-4, 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-Benzoxazolinone, cas is 59-49-4,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of 4a or 4b (1mol equiv.) in anhydrous THF was added TEA (3mol equiv.). The mixture was added drop wise the solution of acyl chlorides (1.1mol equiv.) in anhydrous THF at 0C and stirred at 70C for 6h. The water was added to quench the reaction. The mitxure was extracted with ethyl acetate to afford the crude product that was purified by flash column chromatography on silica gel to yield the target products.

The chemical industry reduces the impact on the environment during synthesis,59-49-4,2-Benzoxazolinone,I believe this compound will play a more active role in future production and life.

Reference：
Article; Zou, Yi; Wang, Yan; Wang, Fang; Luo, Minghao; Li, Yuezhen; Liu, Wen; Huang, Zhangjian; Zhang, Yihua; Guo, Wenjie; Xu, Qiang; Lai, Yisheng; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 199 – 211;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

Name is 5-Methylbenzo[d]oxazole-2(3H)-thione, as a common heterocyclic compound, it belongs to benzoxazole compound, and cas is 22876-22-8, its synthesis route is as follows.

INVENTIVE EXAMPLE 35 5-Methyl-2-(4-methyl-1-homopiperazinyl)benzoxazole 5-Methyl-2-mercaptobenzoxazole (200 mg) was dissolved in chloroform (20 ml), N-methylhomopiperazine (1.24 ml) was added dropwise to the solution and then the mixture was stirred with heating for 2 days. After evaporation of the solvent, the thus obtained mixture was purified by a silica gel column chromatography (methylene chloride_methanol=10:1) to obtain the title compound 5-methyl-2-(4-methyl-1-homopiperazinyl)benzoxazole (124 mg).

22876-22-8, 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.,22876-22-8 ,5-Methylbenzo[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

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

3H-1,3-Benzoxazol-2-one (5.00?g, 37.00?mmol) was dissolved in acetic acid (50?mL) and bromine (1.9?mL, 37.0?mmol) was added dropwise. The reaction mixture was stirred at 20?C for 4?h.The reaction mixture was poured onto ice and the precipitate was collected by filtration, washed with water and air-dried to give a pink powder (7.48?g, 34.8?mmol, 94%). Mp 191.6-192.3?C. 1H NMR (300?MHz, DMSOd6): delta 11.81 (s, 1H), 7.57 (dd, J?=?1.9?Hz, J?=?0.3?Hz, 1H), 7.30 (dd, J?=?8.3?Hz, J?=?1.9?Hz, 1H), 7.04 (dd, J?=?8.3?Hz, J?=?0.3?Hz, 1H). 13C NMR (75?MHz, DMSOd6): delta 154.5, 144.5, 130.3, 126.9, 113.5, 113.2, 111.7. LCMS m/z calc for [M?-?H]+: 211.9, 213.9, found: 211.8, 213.8.

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：
Article; Gay, Marion; Evrard, Caroline; Descamps, Florian; Carato, Pascal; Renault, Nicolas; Coevoet, Mathilde; Eddarkaoui, Sabiha; Baud, Catherine; Larchanche, Paul-Emmanuel; Buee, Luc; El Bakali, Jamal; Vingtdeux, Valerie; Sergeant, Nicolas; Melnyk, Patricia; European Journal of Medicinal Chemistry; vol. 159; (2018); p. 104 – 125;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belongs to benzoxazole compound, name is 5-Methyl-2-aminobenzoxazol, and cas is 64037-15-6, its synthesis route is as follows.

A solution of succinic anhydride (141.1 g, 1.41 mol) and 70 g (about 0.47 mol) of compound of step 1a (70 g, 0.47 mol) in 2500 ml of anhydrous toluene was refluxed for overnight. After that, HATU (10 g, 0.26 mol) and 4-methylmorpholine (41.36 ml, 0.376 mol) were added and the resulting mixture was refluxed for 2-3 hours. TLC showed that the major spot was product (Rf=0.35, acetone_hexane=1:2). After reaction was completed, the solvent was evaporated and the residue was dissolved in about 2000 ml of CH2Cl2. The solution was washed with aqueous NaHCO3. After pH was adjusted to 7-8 and washed with brine, organic phase was separated and dried over MgSO4. Filtration and removal of solvent gave the title compound (98 g) as fine white needle crystalline ESI MS m/e: 231 (M+H)+.

64037-15-6, 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.,64037-15-6 ,5-Methyl-2-aminobenzoxazol, other downstream synthetic routes, hurry up and to see

Reference：
Patent; Wang, Guoqiang; Phan, Ly Tam; Or, Yat Sun; Qiu, Yao-Ling; Niu, Deqiang; Peng, Yulin; Busuyek, Marina; Wang, Yanchun; Nakajima, Suanne; US2006/252710; (2006); A1;,
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.

A mixture of 114-1 (1.00 g, 4.72 mmol), NBS (840 mg, 4.72 mmol), and AIBN (350 mg) in CCl4 (20 mL) is heated at 90 C for 16 h. The reaction is cooled to ambient temperature, diluted with DCM (100 mL), washed with H2O (2 x 75 mL), dried over Na2SO4, filtered and concentrated. The residue is purified by flash chromatography (0- 50% EtOAc in heptane) to give 114-2.

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ABEYWARDANE, Asitha; BRUNETTE, Steven Richard; BURKE, Michael Jason; KIRRANE, Thomas Martin, Jr.; MAN, Chuk Chui; MARSHALL, Daniel Richard; PADYANA, Anil Kumar; RAZAVI, Hossein; SIBLEY, Robert; SMITH KEENAN, Lana Louise; SNOW, Roger John; SORCEK, Ronald John; TAKAHASHI, Hidenori; TAYLOR, Steven John; TURNER, Michael Robert; YOUNG, Erick Richard Roush; ZHANG, Qiang; ZHANG, Yunlong; ZINDELL, Renee M.; WO2014/14874; (2014); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

It is a common heterocyclic compound, the benzoxazole compound, 6-Bromobenzo[d]oxazol-2(3H)-one, cas is 19932-85-5 its synthesis route is as follows.

A mixture of 6-bromo-1 ,3-benzoxazol-2(3H)-one (2 g ; 9.34 mmol) and copper (I ) cyan ide (1 .42 g; 1 5.86 mmol) in 6 m l D M F is heated at 1 50C u nder nitrogen atmosphere for 22 hr. After cooling to room temperature, a solution of 1 .55 g (31 .6 mmol) of sodium cyanide in 32 ml water is added followed by 1 hr stirring. The system is extracted thoroughly with ethyl acetate, washed with brine, dried and concentrated in vacuo to provide 1 .5 g (93 % yield) of the title compound enough pure as to prosecute the syntesis.

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; ALMIRALL, S.A.; AIGUADE BOSCH, Jose; GUAL ROIG, Silvia; PRAT QUINONES, Maria; PUIG DURAN, Carlos; WO2013/68552; (2013); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem