Heterocyclic Building Blocks-Benzoxazole

The important role of 19932-85-5

The chemical industry reduces the impact on the environment during synthesis,19932-85-5,6-Bromobenzo[d]oxazol-2(3H)-one,I believe this compound will play a more active role in future production and life.

19932-85-5, 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. 6-Bromobenzo[d]oxazol-2(3H)-one, cas is 19932-85-5,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

Iodoethane (100 muL, 1 mmol) was added to a mixture of 6-bromo-1,3-benzoxazol-2(3H)-one (Acros, catCC75710DA, 150 mg, 0.70 mmol) and potassium carbonate (0.3 g, 2 mmol) in Acetone (3 mL). The reaction mixture was stirred at 80 C. for 2 h then cooled to room temperature and filtered. The filtrate was concentrated and the residue was purified by flash chromatography on a silica gel column eluting with 0 to 30% EtOAc in Hexanes to give the desired product. LC-MS calculated for C9H9BrNO2 (M+H)+: m/z=242.0. found 242.0.

Reference：
Patent; Incyte Corporation; Wu, Liangxing; Konkol, Leah C.; Lajkiewicz, Neil; Lu, Liang; Xu, Meizhong; Yao, Wenqing; Yu, Zhiyong; Zhang, Colin; He, Chunhong; (107 pag.)US2016/9712; (2016); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

Analyzing the synthesis route of 19219-99-9

The chemical industry reduces the impact on the environment during synthesis,19219-99-9,5-Chloro-2-methylbenzo[d]oxazole,I believe this compound will play a more active role in future production and life.

19219-99-9, 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-Chloro-2-methylbenzo[d]oxazole, cas is 19219-99-9,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

Preparative Example 3; Step A; Commercially available 5-chloro-2-methylbenzoxazole (1.5 g), potassium cyanide (612 mg), dipiperidinomethane (720 muL), palladium diacetate (80 mg) and 1,5-bis-(diphenylphosphino)pentane (315 mg) were dissolved in dry toluene (20 mL), degassed and stirred at 160 C. in a sealed pressure tube under argon. After 24 h the mixture was diluted with ethyl acetate. The organic layer was washed with saturated ammonium chloride and brine, dried (MgSO4), concentrated and purified by column chromatography (silica, cyclohexane/EtOAc, 9:1 to 7:3) to afford the intermediate (372 mg; 26%) as a colourless solid. 1H-NMR (CDCl3) delta=2.63 (s, 3H), 7.48-7.58 (s, 2H), 7.90 (s, 1H).

Reference：
Patent; ALANTOS PHARMACEUTICALS, INC.; US2007/155739; (2007); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

The important role of 132244-31-6

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-Bromobenzo[d]oxazole, 132244-31-6

132244-31-6, 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-Bromobenzo[d]oxazole, cas is 132244-31-6,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To an oven-dried 10 mL vial were added the heteroarene 1 (0.40 mmol, 1.0 equiv), 1-adamantanecarboxylic acid (2; 216 mg, 1.20 mmol, 3.0 equiv), K2HPO4 (209 mg, 1.20 mmol, 3.0 equiv), 9-mesityl-10-methylacridinium perchlorate (8.2 mg, 5.0 mol%), and [Co(dmgH)(dmgH2)Cl2] (11.6 mg, 8.0 mol%). After the vial was capped with a septum, it was evacuated and refilled with N2 for three times before DCE (1.5 mL) and H2O (0.5 mL) were added sequentially. If the heterocyclic substrate 1 was a liquid, it was added at this point. The mixture was degassed and stirred for 24 h under visible light irradiation (Kessil A360N, see Figure S-1 in the Supporting Information). After 24 h, the mixture was diluted with CH2Cl2 (10 mL) and H2O (10 mL), and the phases were separated. The aqueous layer was extracted with CH2Cl2 (2 × 10 mL), the combined organic phases were dried (Na2SO4), and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (n-pentane or n-hexane/Et2O 20:1 to 2:1) affording the corresponding product 3.

Reference：
Article; Koeller, Julian; Gandeepan, Parthasarathy; Ackermann, Lutz; Synthesis; vol. 51; 5; (2019); p. 1284 – 1292;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

Introduction of a new synthetic route about 59-49-4

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.

40.0 g (0.30 mol) of 2-benzoxazolinone were dissolved with stirring at room temperature in 600.0 ml (0.30 mole) of 68% nitric acid. It was then heated to 50 C. and stirred at this temperature for three hours. The reaction was stirred for a further 16 h at room temperature. After completion of the reaction, the mixture was poured into about 2.0 l of ice water, precipitated substance was filtered off, washed neutral and dried. After drying, 6-nitro-3H-1,3-benzoxazol-2-one (39.1 g, 72%) was obtained as a pale yellow solid. 1H-NMR (300 MHz, d6-DMSO): delta=7.25 (d, 1H, 4-H), 8.10 (d, 1H, 5-H), 8.17 (s, 1H, 7-H), 12.43 (br s, 1H, NH).

Reference：
Patent; Henkel AG & Co. KGaA; Gebert-Schwarzwaelder, Antje; Nemitz, Ralph; Kroos, Astrid; Koenen, Annika; (20 pag.)US2019/167551; (2019); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

Share a compound : 177492-52-3

177492-52-3, 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. Benzo[d]oxazol-6-amine, cas is 177492-52-3,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of the appropriate amine (1M-3M, 2 mmol) and the appropriate aldehyde (2.2 mmol) in ethanol (10 mL) was stirred at room temperature for 8 h.

Reference：
Article; Zhang, Da-Jun; Sun, Wen-Fang; Zhong, Zhao-Jin; Gao, Rong-Mei; Yi, Hong; Li, Yu-Huan; Peng, Zong-Gen; Li, Zhuo-Rong; Molecules; vol. 19; 1; (2014); p. 925 – 939;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

Analyzing the synthesis route of 5676-60-8

The chemical industry reduces the impact on the environment during synthesis,5676-60-8,2-Methylbenzo[d]oxazol-6-amine,I believe this compound will play a more active role in future production and life.

5676-60-8, 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]oxazol-6-amine, cas is 5676-60-8,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

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 × 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.

Reference：
Article; Balraju, Vadla; Jogula, Sridhar; Krishna, Vagolu Siva; Meda, Nikhila; Sriram, Dharmarajan; Bioorganic Chemistry; vol. 100; (2020);,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

Analyzing the synthesis route of 1750-45-4

1750-45-4, 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.,1750-45-4 ,5-Chloro-6-hydroxybenzo[d]oxazol-2(3H)-one, other downstream synthetic routes, hurry up and to see

As a common heterocyclic compound, it belongs to benzoxazole compound, name is 5-Chloro-6-hydroxybenzo[d]oxazol-2(3H)-one, and cas is 1750-45-4, its synthesis route is as follows.

6-Hydroxy-5-chlorobenzo [d] oxazol-2 (3H) -one(1.8 g, 10 mmol),3-Bromomethyl-2H-1,2,3-triazole (1.8 g, 11 mmol),A mixture of potassium carbonate (2.8 g, 20 mmol) in acetonitrile (200 mL) was stirred at 70 C for 16 h,The solvent was removed in vacuo and the residue was purified by column chromatography on silica gel eluting with petroleum ether / ethyl acetate 20: 1,To give 3 – [(2H- 1,2,3 -triazol-2-yl) methyl) -5-chloro-6- hydroxybenzo [d] oxazol-2 (3H) -one as an orange solid (2.3 g, 85%)

Reference：
Patent; Mudanjiang Medical School; Li Hailin; Wang Wei; Song Jing; Sun Zhiguo; Han Guangyu; (12 pag.)CN106928212; (2017); A;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

Introduction of a new synthetic route about Benzo[d]oxazol-2-amine

4570-41-6, 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. Benzo[d]oxazol-2-amine, cas is 4570-41-6,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

Example 66: 4-r3-(4-Chloro-phenoxy)-benzyl1-piperazine-1 -carboxylic acid benzooxazol-2-ylamide.; To a solution of benzooxazole-2-ylamine (35.8 mg, 0.267 mmol) in CH2CI2 (6.0 ml_) was added N,N’-disuccinimidyl carbonate (68.4 mg, 0.267 mmol). The reaction mixture was stirred at rt for 6 h, then treated with 1-[3-(4-chloro-phenoxy)- benzyl]-piperazine hydrochloride (100 mg, 0.267 mmol) and diisopropylethylamine (92 mul_, 0.536 mmol) and stirred for an additional 16 h at rt. The reaction mixture was diluted with EtOAc (100 ml_) and extracted with H2O (100 ml_) then saturated aqueous NaCI (50 ml_). The organic layer was dried (MgSO4), and concentrated. The crude residue was purified (FCC, 2 N NH3 in MeOH/DCM) to give 4-[3-(4-chloro- phenoxy)-benzyl]-piperazine-1 -carboxylic acid benzooxazol-2-ylamide (78.0 mg, 63percent). MS (ESI+): calcd for C25H23CIN4O3 m/z 462.15, found 463.5 (M+H)+. 1H NMR (d6-DMSO): 12.13 (br s, 1 H), 7.46-7.39 (m, 3H), 7.36 (t, J = 7.9, 1 H), 7.30 (br s, 1 H), 7.22 (t, J = 7.6, 1 H), 7.18-7.11 (m, 2H), 7.04 (d, J = 9.0, 2H), 7.00 (br s, 1 H), 6.94- 6.91 (m, 1 H), 3.73-3.54 (br m, 4H), 3.50 (s, 2H), 2.40-2.31 (m, 4H).

Reference：
Patent; JANSSEN PHARMACEUTICA NV; BREITENBUCHER, J., Guy; KEITH, John, M.; TICHENOR, Mark, S.; CHAMBERS, Alison, L.; JONES, William, M.; HAWRYLUK, Natalie, A.; TIMMONS, Amy, K.; MERIT, Jeffrey, E.; SEIERSTAD, Mark, J.; WO2010/68453; (2010); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

Extracurricular laboratory: Synthetic route of 19932-85-5

Example 3: Scheme B2; To a solution of B2.1 (1 equiv., 23 mmol, 5.0 g) in acetone (230 ml) were successively added potassium carbonate (1.5 equiv., 35 mmol, 5.0 g) and iodomethane (1.2 equiv., 28 mmol, 4.0 g); the mixture was stirred at room temperature for 4 h. The acetone solvent was partially concentrated under reduced pressure; this mixture was poured on a IN aqueous HCl solution, filtered and successively washed with water, isopropanol and isopropyl ether, affording a pink powder B2.2 (4.22 g, yield = 79%, purity (LC) = 99%).

Reference：
Patent; TIBOTEC PHARMACEUTICALS LTD.; WO2008/37784; (2008); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

The important role of 41014-43-1

The chemical industry reduces the impact on the environment during synthesis,41014-43-1,2-(Chloromethyl)benzo[d]oxazole,I believe this compound will play a more active role in future production and life.

41014-43-1, 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-(Chloromethyl)benzo[d]oxazole, cas is 41014-43-1,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

Step E Preparation of 3-[(benzoxazol-2-yl)methoxy]-2-methoxy-5-ethyl-6-methylpyridine A quantity of 60% sodium hydride in mineral oil (24 mg, 0.6 mmol) was added to a solution of 2-methoxy-3-hydroxy-5-ethyl-6-methylpyridine (77 mg, 0.46 mmol) in dry dimethylformamide (2 mL). After gas evolution ceased, 2-(chloromethyl) benzoxazole (100 mg, 0.6 mmol) was added and the reaction mixture warmed at 60 C. for one hour. The reaction was then cooled, diluted with diethyl ether, the ether extract washed with water, dried (Na2 SO4), filtered and evaporated to give 151 mg of crude mixture. This mixture was flash chromatographed on silica gel, eluding with 0.5% methanol/chloroform. Combined appropriate fractions gave 46 mg (32%) of oily product.

Reference：
Patent; Merck & Co., Inc.; US5308854; (1994); A;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem