Heterocyclic Building Blocks-Benzoxazole

Name is 2-(Bromomethyl)benzo[d]oxazole, as a common heterocyclic compound, it belongs to benzoxazole compound, and cas is 73101-74-3, its synthesis route is as follows.

EXAMPLE 5 Various compounds of the formula: STR10 as listed in the following Table 4 were prepared in substantially the same manner as in Examples 3 and 4. example 6 benzoxazole-2-methanesulfonyl chloride: To a solution of 3.0 g of 2-bromomethylbenzoxazole [prepared according to the procedures described in Belgian Pat. No. 624,463] in 40 ml of methanol was added a solution of 1.9 g of sodium sulfite in 40 ml of water. The mixture was heated with stirring at 60 C. for 6 hours and concentrated under reduced pressure to give crude sodium benzoxazole-2-methanesulfonate (4.5 g).

73101-74-3, 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.,73101-74-3 ,2-(Bromomethyl)benzo[d]oxazole, other downstream synthetic routes, hurry up and to see

Reference：
Patent; Dainippon Pharmaceutical Co., Ltd.; US4172896; (1979); A;,
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Name is 5-Chlorobenzo[d]oxazole-2(3H)-thione, as a common heterocyclic compound, it belongs to benzoxazole compound, and cas is 22876-19-3, its synthesis 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 < 20C. DMF (4.59 g, 62.8 mmol) was added dropwise. A vigorous gas formation was observed and the suspension turned into a solution halfway throughout the addition. The reaction mixture was stirred for 20 minutes. Two additional aliquots oxalyl chloride (1 : 0.20g, 1.35 mmol; 2: 0.40 g, 2.70 mmol) were added and the reaction mixture was stirred for 1.5 hours. HPLC indicated complete conversion of 2-mercapto-5-chlorobenzoxazol into 2,5- Dichlorobenzoxazol . 22876-19-3, 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.,22876-19-3 ,5-Chlorobenzo[d]oxazole-2(3H)-thione, other downstream synthetic routes, hurry up and to see

Reference：
Patent; SANDOZ AG; BARTH, Roland; HOeFERL-PRANTZ, Kathrin; RICHTER, Frank; WIDSCHWENTER, Gerhard; (166 pag.)WO2016/20405; (2016); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

Name is 2-Methylbenzo[d]oxazol-6-amine, as a common heterocyclic compound, it belongs to benzoxazole compound, and cas is 5676-60-8, its synthesis route is as follows.

2,2,2-trifluoro-N-(2-methylbenzo[d]oxazol-6-yl)acetamide A solution of 2-methylbenzo[d]oxazol-6-amine (8.4 g, 56.7 mmol) in pyridine (80 mL) at 0 C. was treated with TFAA (19.8 mL, 141.0 mmol) and stirred at rt for 4 h. The reaction mixture was diluted with water (100 mL) and the product extracted with EtOAc (3*100 mL). The organics were washed with brine, dried over Na2SO4, and concentrated to obtain the crude 2,2,2-trifluoro-N-(2-methylbenzo[d]oxazol-6-yl)acetamide (15.0 g), (MS: ESI +ve, 245.20 [M-H]); 1H NMR: (400 MHz, DMSO) delta: 2.61 (s, 3H), 7.61-7.56 (m, 1H), 7.69-7.67 (d, J=8.4, 1H), 8.04-8.04 (d, J=2, 1H), 11.45 (s, 1H).

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; FLATLEY DISCOVERY LAB; Cole, Bridget M.; US2014/274933; (2014); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

Name is 5-Chlorobenzo[d]oxazole-2(3H)-thione, as a common heterocyclic compound, it belongs to benzoxazole compound, and cas is 22876-19-3, its synthesis route is as follows.

INVENTIVE EXAMPLE 41 5-Chloro-2-(4-methyl-1-homopiperazinyl)benzoxazole 5-Chloro-2-mercaptobenzoxazole (1 g) was dissolved in toluene (50 ml), N-methylhomopiperazine (3.3 ml) was added dropwise to the solution and then the mixture was stirred with heating for 2 hours. After evaporation of the solvent, the thus obtained mixture was purified by a silica gel column chromatography (methylene chloride_methanol=20:1) to obtain the title compound 5-chloro-2-(4-methyl-1-homopiperazinyl)-benzoxazole (882 mg).

22876-19-3, 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.,22876-19-3 ,5-Chlorobenzo[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

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 a flame-dried reaction tube was added 1,3-azoles (0.5 mmol, 1.0 eq), 1,10-phenoline (0.5 mmol, 1.0 eq), LiOtBu (1.0 mmol, 2.0 eq), CuBr2 (0.10 mmol, 0.2 eq) and iodine (0.75 mmol, 1.5 eq). Dry 1,4-dioxane (2 mL) was added to the mixture and the mixture was heated to 80C by putting the reaction tube to a preheated oil bath until the products were not increased. The mixture was cooled to room temperature and filtered through a short pad of silica gel. The silica gel was washed with EtOAc (20 mL) and the combined the organic phase was concentrated under reduced pressure to give a residue which was purified by silica gel column chromatography to afford the iodination product.

The chemical industry reduces the impact on the environment during synthesis,132244-31-6,5-Bromobenzo[d]oxazole,I believe this compound will play a more active role in future production and life.

Reference：
Article; Zhao, Xia; Ding, Fang; Li, Jingyu; Lu, Kui; Lu, Xiaoyu; Wang, Bin; Yu, Peng; Tetrahedron Letters; vol. 56; 3; (2015); p. 511 – 513;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

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

The bromo compound R (1.0 g, 4.67 mmol) was taken in an oven-dried RB equipped with magnetic stir-bar and dissolved in anhydrous THF (9 mL). The solution was cooled to -78 C. and MeMgBr (1.8 mL) was added slowly. The mixture was stirred for 45 min and anhydrous THF (37.5 mL) was added slowly to maintain the internal temperature at -50 C. After the solution was cooled back to -78 C., t-BuLi (10.6 mL, 9.8 mmol, 1.6 M in pentane) was added dropwise. Next, DMF (2.2 mL, 28.1 mmol) was added slowly to the yellow solution and the dry-ice bath was removed after 15 min. After 2 h, the reaction was quenched with water and the THF was removed under vacuo on a rotary evaporator. The residue was dissolved in ethyl acetate and washed with 1N HCl (5 mL). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3×5 mL). The organic layers were combined, dried over Na2SO4 and concentrated under vacuo on a rotary evaporator. The crude was first recrystallized from hexanes/ethyl acetate and then purified via gradient silica gel column chromatography using a mixture of hexanes and ethyl acetate (10:1 to 1:1) to obtain the desired aldehyde S as a white solid (500 mg, 66%). 1H NMR (500 MHz, CDCl3): delta 9.85 (s, 1H), 7.66 (dd, J=7.9 Hz, 1.2 Hz, 1H), 7.63 (s, 1H), 7.11 (d, J=7.9 Hz, 1H). 13C NMR (125 MHz, CDCl3): delta 190.9, 155.2, 144.1, 135.9, 131.4, 128.2, 109.6, 109.5

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; DUTTA, Aloke K.; US2014/309427; (2014); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

151230-42-1, 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. 6-Bromo-2-methylbenzo[d]oxazole, cas is 151230-42-1,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

[001255] Part 2: A mixture of 6-bromo-2-methylbenzo[d]oxazole (1.06 g, 5.0 mmol), 4,4,4?,4?,5 ,5 ,5?,5?-octamethyl-2,2?-bi( 1,3 ,2-dioxaborolane) (1.40 g, 5.5 mmol), KOAc (1.47 g, 15 mmol) and Pd(dppf)C12.CH2C12 (122 mg, 0.15 mmol) in dioxane ( 8 mL) was degassed and heated under N2 at 85 C. After 15 hours, the mixture was diluted with EtOAc, filtered through celite and concentrated. The residue was chromatographed to give 2-methyl-6-(4,4,5,5- tetramethyl- 1,3 ,2-dioxaborolan-2-yl)benzo [d]oxazole as a light orange solid (1 .30 g, 100%), MS m/z 260.4 [M+H].

The chemical industry reduces the impact on the environment during synthesis,151230-42-1,6-Bromo-2-methylbenzo[d]oxazole,I believe this compound will play a more active role in future production and life.

Reference：
Patent; PTC THERAPEUTICS, INC.; F. HOFFMANN-LA ROCHE AG; QI, Hongyan; CHOI, Soongyu; DAKKA, Amal; KARP, Gary, Mitchell; NARASIMHAN, Jana; NARYSHKIN, Nikolai; TURPOFF, Anthony, A.; WEETALL, Maria, L.; WELCH, Ellen; WOLL, Matthew, G.; YANG, Tianle; ZHANG, Nanjing; ZHANG, Xiaoyan; ZHAO, Xin; GREEN, Luke; PINARD, Emmanuel; RATNI, Hasane; WO2013/119916; (2013); A2;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

136992-95-5, 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. Benzo[d]oxazol-7-amine, cas is 136992-95-5,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 6-Bromo-4-chloroquinoline (1.0 equiv.) and 3,4,5-trimethoxyaniline (1.1 equiv.) were suspended in ethanol (10 mL) and refluxed for 18 h. The crude mixture was purified by flash chromatography using EtOAc:hexane followed by 1-5% methanol in EtOAc, solvent was removed under reduced pressure to afford the desired product (1, 8-11, 13-31, and 33-43).

The chemical industry reduces the impact on the environment during synthesis,136992-95-5,Benzo[d]oxazol-7-amine,I believe this compound will play a more active role in future production and life.

Reference：
Article; Asquith, Christopher R.M.; Bennett, James M.; Su, Lianyong; Laitinen, Tuomo; Elkins, Jonathan M.; Pickett, Julie E.; Wells, Carrow I.; Li, Zengbiao; Willson, Timothy M.; Zuercher, William J.; Molecules; vol. 24; 22; (2019);,
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

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