Month: June 2021

As a common heterocyclic compound, it belongs to benzoxazole compound, name is Benzo[d]oxazol-6-amine, and cas is 177492-52-3, its synthesis route is as follows.

General procedure: HBTU (147 mg, 0.39 mmol) and DIPEA (0.13 g, 1.0 mmol) were added to a solution of 4-(quinolin-2-ylmethoxy)benzoic acid (100 mg, 0.35 mmol) in DMF (5 mL), and the mixture was stirred at room temperature for 30 min N-methylaniline (38 mg, 0.35 mmol) was added, and the resulting mixture was stirred at room temperature for 12 h. Water (15 mL) was added, the resultant mixture was extracted with EtOAc (15 mL). The organic layer was separated, dried over Na2SO4, filtered, and concentrated under vacuum. The residue was purified by preparative HPLC to afford the title compound as an off white solid (11% yield).

177492-52-3, 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.,177492-52-3 ,Benzo[d]oxazol-6-amine, other downstream synthetic routes, hurry up and to see

Reference：
Article; Kilburn, John Paul; Kehler, Jan; Langgard, Morten; Erichsen, Mette N.; Leth-Petersen, Sebastian; Larsen, Mogens; Christoffersen, Claus Tornby; Nielsen, Jacob; Bioorganic and Medicinal Chemistry; vol. 21; 19; (2013); p. 6053 – 6062;,
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.

General procedure: The compound 14?16 (1 mmol) was dissolved in dry ethanol (5 mL). To this, benzoxazol-2-amine (11)/benzothiazol-2-amine (12)/1H-benzimidazol-2-amine (13) (1.3 mmol) and a catalytic amount of methylsulfonic acid (0.2mL) were added and heated at 70 °C for 3?5 h. The reaction mixture was cooled and diluted with water (15 mL). The resultant solid was filtered, dried and recrystallized from 2-propanol.

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：
Article; Seenaiah; Reddy, P. Ramachandra; Reddy, G. Mallikarjuna; Padmaja; Padmavathi; Siva Krishna; European Journal of Medicinal Chemistry; vol. 77; (2014); p. 1 – 7;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

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

(1) Synthesis of 4beta-S-(6-chlorobenzoxazole-2)-podophyllotoxin: 414 mg (1 mmol) of podophyllotoxin,201 mg (1 mmol) of 6-chlorobenzoxazole-2-thiol, dried under vacuum for 1 h, using 15 mL of trifluoroacetic acid as solvent in ice bath.The mixture was stirred under vacuum for 1 to 3 hours, and chloroform acetone was used as a developing solvent to detect the end point of the reaction. Adding the reaction system to 20 to 50 times the volumeIn deionized water, the filter cake was collected by filtration and washed to obtain a crude product.

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; Tang Yajie; Zhao Wei; (23 pag.)CN108285456; (2018); A;,
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.

General procedure: A mixture of intermediate compound N-(3-(1H-tetrazole-5-yl) phenyl)-2-chloroacetamideand benzo[d]oxazole-2-thiol or benzo[d]thiazole-2-thiol or 2-mercapto benzimidazoles in anequimolar amount were taken and refluxed with acetone (20 mL) in the presence of K2CO3for 24 hr. The reaction was monitored by TLC and on completion of the reaction, an excessof solvent was evaporated at room temperature and the reaction mixture was diluted withwater (about 200 mL). The diluted hydrochloric acid was added to precipitate the productwhich was further filtered and thoroughly washed with cold water.

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：
Article; Maheshwari, Neelesh; Karthikeyan, Chandrabose; Bhadada, Shraddha V.; Verma, Amit K.; Sahi, Chandan; Moorthy, N.S. Hari Narayana; Trivedi, Piyush; Bioorganic Chemistry; vol. 92; (2019);,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

81900-93-8, 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. 4-Aminobenzo[d]oxazol-2(3H)-one, cas is 81900-93-8,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

Example 26: 1-(2-chloro-4-(trifluoromethyl)benzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea (scheme 1) Preparation of 1-(2-chloro-4-(trifluoromethyl)benzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea Commercially available 2-chloro-4-trifluoromethylbenzylamine (572 mg, 2.7 mmol) was dissolved in 20ml of AcOEt and at 0C triphosgene (809 mg, 2.7 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and dissolved in 5 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (5 ml) of compound 1b (270 mg, 1.8 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 70 mg of a white solid. Yield = 10% 1HNMR (DMSO, 400 MHz) delta 4.45 (2H, d, J = 6 Hz), 6.97 (2H, d, J = 4.4 Hz), 7.07 (2H, m), 7.63 (1H, d, J = 8 Hz), 7.74 (2H, d), 7.86 (1H, s), 8.61 (1H, bs), 10.90 (1H, bs); [M+1] 386.6 (C16H11ClF3N3O3 requires 385.7).

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 4-Aminobenzo[d]oxazol-2(3H)-one, 81900-93-8

Reference：
Patent; Pharmeste S.r.l.; EP2377850; (2011); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

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.

Intermediate 4. 2- oxo-2,3-dihydro-1 ,3-benzoxazole-6-carbaldehyde To a suspension of 6-bromobenzo[d]oxazol-2(3H)-one (6.12g, 28.6mmol) in THF (60ml_) was added, at -78 C and under argon atmosphere, methylmagnesium bromide (10.6ml_ of a 3M solution in diethyl ether, 31 .8mmol) and the reaction mixture was stirred at this temperature fro 30 min. The, an additional amount of THF (240 mL) was added at a rate that the internal temperature was below -50 C. Then, tert-butyllithium (60.6ml_ of a 1.7 M solution in pentane, 103mmol) was slowly added and stirred for 45 min at -78 C. To the yellow suspension DMF (13.4ml_, 181 mmol) was then added, and the reaction mixtures was allowed to warm up to room temperature and stirring wasa continued for 3 additional hours. Water (300ml_) was then added to the crude mixture and the organic solvent was removed under reduced pressure. To the remaining aqueous phase, ethyl acetate (500ml_) and 1 N HCI (150ml_) were added and the the mixture was vigorously stirred and the organic phase was separated. The aqueous phase was further extracted with ethyl acetate (3 x 100 mL) and the combined organic extracts were washed with water, brine, dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to yield the title compound (4.75g, 96%, 94% purity by UPLC). The compound was used as this without further purification. LRMS (m/z): 162 (M-1 )-

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 6-Bromobenzo[d]oxazol-2(3H)-one, 19932-85-5

Reference：
Patent; ALMIRALL, S.A.; PUIG DURAN, Carlos; AIGUADE BOSCH, Jose; GUAL ROIG, Silvia; PRAT QUINONES, Maria; (149 pag.)WO2016/46390; (2016); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

It is a common heterocyclic compound, the benzoxazole compound, 2-Methylbenzo[d]oxazole-6-carbaldehyde, cas is 864274-04-4 its synthesis route is as follows.

To a solution of compound 66 (50 mg, 174.6 imo1, 1 eq) in 1 mL of MeOH was added 2-methyl-1,3-benzoxazole-6-carbaldehyde (30.9 mg, 192.1 imol, 1.1 eq) and HOAc (1.1 mg,17.5 imol, 0.1 eq). The mixture was stirred for 0.5 hour at 25°C. Then NaBH3CN (16.5 mg, 261.9 imol, 1.5 eq) was added and the mixture was stirred for 11.5 hours. The reaction mixture was filtered and the filtrate was purified by prep-HPLC (neutral condition) to get 30.9 mg ofcompound 530 (40.6percent yield, 99.1percent purity) as a white solid.?H NMR (400MHz, CHLOROFORM-cl) oe ppm 11.34 – 11.21 (m, 1H), 7.77 – 7.70 (m, 1H),7.53-7.48 (m, 2H), 7.42 (d,J=5.5 Hz, 1H), 7.27 (brs, 2H), 7.21- 7.19(m, 1H), 5.91 -5.85 (m,1H), 4.54 (br t, J=11.9 Hz, 1H), 4.24 (q, J=6.9 Hz, 1H), 3.91 – 3.89 (m, 2H), 3.55 (q, J7.0 Hz,1H), 2.79-2.76 (m, 1H), 2.57 (s, 3H), 2.31 -2.11 (m, 1H), 1.97- 1.82 (m, 3H), 1.54- 1.47 (m,3H), 1.29 (t, J=7.0 Hz, 3H), 1.27 – 1.09 (m, 1H).LCMS (ESI+): m/z 432.2 (M+H)

864274-04-4, 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.,864274-04-4 ,2-Methylbenzo[d]oxazole-6-carbaldehyde, other downstream synthetic routes, hurry up and to see

Reference：
Patent; AQUINNAH PHARMACEUTICALS, INC.; BURNETT, Duane, A.; VACCA, Joseph, P.; (310 pag.)WO2018/119395; (2018); 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.

In a reactor equipped with exhaust gas absorption, 27.0 g of benzoxazolone (molecular weight 135.1, 0.20 mol) was added, 245.3 g of phosphorus oxychloride (molecular weight 153.3, 1.6 mol), After stirring at room temperature for 30 minutes, Cool down to around 0 C, The chlorine gas is reacted, and the chlorine gas flow rate is about 20.0g per hour. The access time is about 3h (molecular weight 71, 0.21mol), The benzoxazolone content is detected during the chlorine process, When the benzoxazolone content is less than 1%, it is considered to be the end of chlorine.

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; Jiangsu Zhongqi Technology Co., Ltd.; Jin Yucun; Zhang Pu; Wang Fengyun; Hou Yuanchang; (7 pag.)CN109553588; (2019); A;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

81900-93-8, 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. 4-Aminobenzo[d]oxazol-2(3H)-one, cas is 81900-93-8,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

Example 56: 2-(4-(trifluoromethyl)phenyl)-N-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)acetamide (scheme 10) Preparation of 2-(4-(trifluoromethyl)phenyl)-N-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)acetamide 4-trifluoromethylphenylacetic acid (453 mg, 2.2 mmol) was dissolved in 20 ml of THF and at 0C DEPC (0.43 ml, 1.3equiv) and amine 1b (400 mg, 2.66 mmol) were added to the solution. The mixture was warmed at 80C overnight, then 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 using AcOEt as eluant gave 360 mg of a white solid. Yield = 48% 1HNMR (DMSO, 200 MHz) delta 3.80 (2H, s), 7.10 (3H, m), 7.58 (2H, d, J = 8.4 Hz), 7.70 (2H, d, J = 8.2 Hz), 10.06 (1H, bs), 11.14(1H, bs); [M+1] 336.9 (C16H11F3N2O3 requires 336.3).

The chemical industry reduces the impact on the environment during synthesis,81900-93-8,4-Aminobenzo[d]oxazol-2(3H)-one,I believe this compound will play a more active role in future production and life.

Reference：
Patent; Pharmeste S.r.l.; EP2377850; (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.

Intermediate 1.3-al IyI-2-oxo-2,3-dihydro-1 ,3-benzoxazole-6-carbonitrileTo a solution of 2-oxo-2,3-dihydrobenzo[d]oxazole-6-carbonitrile (210mg, 1.31 mmol, that product was synthesized by a mixture of 6-bromo-1 ,3-benzoxazol-2(3H)-one (2 g; 9.34 mmol) and copper (I) cyanide (1.42 g; 15.86 mmol) in 6 ml DMF, heated at 150C under 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 vacuum) in acetonitrile (4mL) was added potassium carbonate (362mg, 2.62mmol) and potassium iodide (43mg, 0.26mmol) in a sealed tub. Then 3- bromoprop-1-ene (0.9mL, 10.4mmol) was added to the reaction. The mixture was stirred overnight at 70C. The solid residue was filtrated through Celite. The solvent of the filtrate was removed under reduced pressure and the crude obtained was treated with ether giving a solid (1 50mg, 57% yield), which was used in the next step without further purification.LRMS (m/z): 201 (M+1)+.

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.; SOLE FEU, Laia; CARRANCO MORUNO, Ines; AIGUADE BOSCH, Jose; PUIG DURAN, Carlos; FONQUERNA POU, Silvia; WO2014/95920; (2014); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem