Category: benzoxazole

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.

To a solution of the compound of Preparation A (0.348 g; l . lmmol) and 6-bromobenzo[< Joxazol-2(3H)-one (prepared as described in EP 1988077, 0.214 g; lmmol) in DMF (4.2 mL) was added K2C03 (0.212g, 1.53mmol). The reaction proceeded at 60C for 16h. Water (20 mL) was added and the resulting mixture was extracted three times with EA (3 x 20 mL). The evaporation residue was purified by CC (EA-Hept) to afford the title compound (0.396 g; 88% yield) as an orange solid. 1H NMR (d6-DMSO) delta 7.69 (d, J = 1.8 Hz, 1H); 7.47 (dd, J = 1.8, 8.3 Hz, 1 H); 7.30 (d, J = 8.3 Hz, 1H); 4.00-3.91 (overlapped m, 1H); 3.91-3.81 (overlapped m, 1H); 3.1 1 (s, 3H); 2.66-2.56 (m, 1H); 2.19-2.10 (m, 1H); 1.58 (s, 3H); 1.35 (s, 9H). MS (ESI, m/z): 448.04 [M+H+] for Ci7H22N06BrS; tR = 0.92 min. 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; ACTELION PHARMACEUTICALS LTD; CHAPOUX, Gaelle; DIETHELM, Stefan; GAUVIN, Jean-Christophe; PANCHAUD, Philippe; SURIVET, Jean-Philippe; (90 pag.)WO2017/37039; (2017); A1;,
Benzoxazole – Wikipedia
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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.

To a solution of 6-bromo-3H-benzoxazol-2-one (15 g; ca. 0.07 mol, containing 8-9% 3H-benzooxazol-2-one) and triethylamine (11.1 mL, 0.08 mol) in DCM (250 mL) was added trityl chloride (21.5 g, 0.08 mol). The solution was stirred at room temperature for 18 h and was then washed with distilled water (3 x 250 mL), brine (250 mL) and dried (MgSO4), filtered and evaporated to give an off-white colored solid. The product was dissolved in refluxing EtOAc then allowed to cool to room temperature with constant stirring for several hours. The solids were collected (21.16 g) and the filtrate was concentrated until precipitation occurred, re-heated (reflux) for several hours and allowed to cool with stirring to encourage a second crystallization (7.88 g).

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; AVENTIS PHARMACEUTICALS INC.; WO2006/86705; (2006); 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.

A reactor was charged with l,3-benzoxazol-2(3H)-one (309 mg) and a 2.5M solution of sodium hydroxide (1.5 g) in water (15 ml). The reactor heated to 100 C and held for 16 hours. The reaction mixture was cooled to ambient temperature then acidified to pH 1 with concentrated hydrochloric acid. The organics were then extracted with ethyl acetate (20 ml). The aqueous phase was basified with 10% aqueous sodium bicarbonate solution to pH 9 and then the organics were extracted with ethyl acetate (3 x 20 ml). The combined organic phase was dried (MgS04), filtered and reduced to an oil by rotary evaporation. This was purified by flash chromatography, eluting with n-hexane and ethyl acetate.Appropriate fractions were collected for the product peak and were reduced by rotary evaporation to obtain the desired product as orange oil (180 mg, 72%). The structure was confirmed as 2-aminophenol by 1H NMR

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：
Patent; NEDERLANDSE ORGANISATIE VOOR TOEGEPAST-NATUURWETENSCHAPPELIJK ONDERZOEK TNO; CROCKATT, Marc; URBANUS, Jan Harm; KONST, Paul Mathijs; DE KONING, Martijn Constantijn; (58 pag.)WO2016/114668; (2016); A1;,
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Benzoxazole | C7H5NO – PubChem

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

General procedure: In the vessel of a microwave reactor, 12 (400 mg, 1.13 mmol), 2-aminopyridine (318 mg, 3.38 mmol), Pd2(dba)3 (51.6 mg,56.4 lmol), 2-dicyclohexylphosphino-20,40,60-triisopropyl-1,10-biphenyl (26.9 mg, 56.4 lmol), and K2CO3 (312 mg, 2.25 mmol)were suspended in t-BuOH (3 mL). The vessel was then sealed,and the mixture was reacted at 130 C for 1 h under microwaveirradiation. After cooling to room temperature, the mixture wasextracted with CHCl3/MeOH (4:1), and washed with brine. Theorganic layer was separated, dried over MgSO4, and concentratedunder reduced pressure. The residue was purified by NH silicagel column chromatography (CHCl3/MeOH = 100:0 to 90:10) togive the title compound (362 mg, 78%). 1H NMR (400 MHz,DMSO-d6) d: 1.27-1.38 (2H, m), 1.41 (9H, s), 1.95-2.02 (2H, m),2.96-3.10 (2H, m), 3.43-3.53 (1H, m), 3.80-3.88 (2H, m), 6.83-6.87 (1H, m), 7.07 (1H, br), 7.22 (1H, s), 7.62-7.66 (2H, m), 7.80(1H, br), 8.20-8.22 (1H, m), 8.40 (1H, s), 8.70 (1H, d, J = 7.2 Hz),9.47 (1H, s). MS (ESI) m/z: 413 (M+H)+.

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：
Article; Nakajima, Yutaka; Aoyama, Naohiro; Takahashi, Fumie; Sasaki, Hiroshi; Hatanaka, Keiko; Moritomo, Ayako; Inami, Masamichi; Ito, Misato; Nakamura, Koji; Nakamori, Fumihiro; Inoue, Takayuki; Shirakami, Shohei; Bioorganic and Medicinal Chemistry; vol. 24; 19; (2016); p. 4711 – 4722;,
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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.

General procedure: A 25 mL two-neck round-bottomed flask was charged with 2-aminobenzothiazole (1a, 180 mg,1.2 mmol), methyl acetoacetate (2a, 108 muL, 1.0 mmol), in 3 mL of CBrCl3/MeCN 1:9 (v/v) solvent mixture. KOt-Bu(224 mg, 2.0 mmol) was added slowly at room temperature and the reaction mixture was stirred under reflux for 16 h. Upon completion, the reaction mixture was diluted with 30 mL of ethyl acetate, filtered through a short pad of silica gel and washed down with an additional 60 mL ethyl acetate. The filtrate was washed with distilled water (3 × 30 mL) and the organic phase was dried with anhydrous Na2SO4. After filtration,the solvent was removed by rotary evaporation and the residue was purified by column chromatography using hexane and ethyl acetate (v/v = 8:1) as eluent to afford 3a with 84percentyield.

The chemical industry reduces the impact on the environment during synthesis,4570-41-6,Benzo[d]oxazol-2-amine,I believe this compound will play a more active role in future production and life.

Reference：
Article; Roslan, Irwan Iskandar; Ng, Kian-Hong; Chuah, Gaik-Khuan; Jaenicke, Stephan; Beilstein Journal of Organic Chemistry; vol. 13; (2017); p. 2739 – 2750;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

It is a common heterocyclic compound, the benzoxazole compound, 5-Nitro-2,3-dihydro-1,3-benzoxazol-2-one, cas is 3889-13-2 its synthesis route is as follows.

EXAMPLE 3 8-(5-Nitro-2-oxo-benzoxazolin-3-yl)-caprylic acid methyl ester The product is produced as described in example 1 from 6 g. of NaH (80% suspension in mineral oil), 36 g. of 5-nitrobenzoxazolin-2-one (produced in usual manner by reacting 2-amino-4-nitrophenol-hydrochloride with phosgene), 400 cc. of DMF, 47.4 g. of 8-bromo caprylic acid methyl ester and 6 g. of NaJ. Yield: 25 g. Fp.: 50 to 51 C. IR (film): 1780 and 1730 cm-1.

3889-13-2, 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.,3889-13-2 ,5-Nitro-2,3-dihydro-1,3-benzoxazol-2-one, other downstream synthetic routes, hurry up and to see

Reference：
Patent; A. Nattermann & Cie GmbH; US4377695; (1983); A;,
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.

To a solution of 3-icHcvl i>ymzx>io 3,4-(: jp rinij.din–4-aoiine (2,0 g, 7.7 mmol) and benzo[?]osazol-2-ansne (3.0 g. l i .5 ninioii in VyV dinietoylfofmamkle (20 mL) was added a solution of NaOH (0.61 g, 15,3 mmol) in water (1.0 mL). The reaction mixture was purged with nitrogen atmosphere and , ‘ (bi.sdipheny.ip.oospm^o)fen:ocenepaJjadiiini(li) dtc oride (Pd(dppf)C (0.56 g, 0.76 nrmol) s slowly added at room temperature followed by heating at 120 °C for 1 hours. The reactioii mixture was cooled, poured into ice water and was extracted wit ethyl acetate. The combined organic layer extracts were dried over anhydrous NajSO,;, filtered, and concentrated in vacuo to give a crude oil which was purified by column cinematography on silica gel (100-200 mesh), eliding with 80percent ethyl acetate: hexanes mixture to afford the title compound (0.32 g, 16percent} as a tight brown solid. NM 400 MHz): 5 13.56 is. iH>, 8.21 is. IH), 7.56 (d, J = 16.S Hz, 2H), (0920) 7.43 (dd, J, 2l .0 Hz, ^ 1.2 Hz, 2H), 7.23 (dd, J, 6.4 Hz. /> = 1.6 Hz, 1 H) 1XMS (retention time 3.6 minutes, m/e 268 |M+1) 97.5percent), Capcell pack CI 8 150*4,6, 3 mu column at 254 nm.

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; SABILA BIOSCIENCES LLC; MANSOUR, Tarek, S.; EVANS, Collen, E.; (156 pag.)WO2018/49127; (2018); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

64037-15-6, 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-Methyl-2-aminobenzoxazol, cas is 64037-15-6,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

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 (100 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

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-Methyl-2-aminobenzoxazol, 64037-15-6

Reference：
Patent; Wang, Guoqiang; Phan, Ly Tam; Or, Yat Sun; Qiu, Yao-ling; Niu, Deqiang; Peng, Yulin; Busuyek, Marina; Wang, Yanchun; Nakajima, Suanne; US2006/252712; (2006); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belongs to benzoxazole compound, name is 5-Bromobenzo[d]oxazole, and cas is 132244-31-6, its synthesis route is as follows.

10.0 grams (g) (50.5 millimoles, mmol) of 5-bromobenzo[d]oxazole, 15.4 g (60.6 mmol) of bis(pinacolato)diboron, 2.06 g (2.52 mmol) of PdCl2(dppf)·CH2Cl2, and 14.9 g (152 mmol) of potassium acetate were dissolved in 168 milliliters (mL) of dimethylformamide (DMF), and stirred at a temperature of 100 C. for 20 hours. After the reaction was completed, the reaction product was cooled to room temperature and filtered through silica gel under reduced pressure, and a filtrate was concentrated under reduced pressure. The product obtained therefrom was separated by silica gel column chromatography. The product was recrystallized with dichloromethane (DCM)/n-hexane as an eluent to obtain 8.91 g (yield: 72%) of Intermediate (A). (0346) LC-Mass (calc: 245.12 g/mol, found: M+1=246 g/mol).

132244-31-6, 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.,132244-31-6 ,5-Bromobenzo[d]oxazole, other downstream synthetic routes, hurry up and to see

Reference：
Patent; Samsung Electronics Co., Ltd.; Samsung SDI Co., Ltd.; JUNG, Yongsik; KWON, Eunsuk; MIN, Minsik; BAE, Hyejin; RAI, Virendra Kumar; SON, Jhunmo; Lee, Hasup; KIM, Jongsoo; KIM, Joonghyuk; (340 pag.)US2019/36039; (2019); 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