Heterocyclic Building Blocks-Benzoxazole

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.

EXAMPLE 251A 6-bromo-1,3-benzoxazol-2(3H)-one A mixture of 2-benzoxazolinone (3.00 g, 22.2 mmol), 1,3-dibromo-5,5-dimethylhydantoin (3.49 g, 12.2 mmol), and trifluoromethanesulfonic acid (5.00 g, 33.3 mmol) in dichloromethane (100 mL) at room temperature was protected from light, stirred for 1 hour, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 50% ethyl acetate/hexanes to provide the desired product.

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-Benzoxazolinone, 59-49-4

Reference：
Patent; Augeri, David J.; Baumeister, Steven A.; Bruncko, Milan; Dickman, Daniel A.; Ding, Hong; Dinges, Jurgen; Fesik, Stephen W.; Hajduk, Philip J.; Kunzer, Aaron R.; McClellan, William; Nettesheim, David G.; Oost, Thorsten; Petros, Andrew M.; Rosenberg, Saul H.; Shen, Wang; Thomas, Sheela A.; Wang, Xilu; Wendt, Michael D.; US2002/55631; (2002); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

As a common heterocyclic compound, it belongs to benzoxazole compound, name is 6-Nitrobenzo[d]oxazole, and cas is 17200-30-5, its synthesis route is as follows.

General procedure: A mixture of VNU-11(Hf) (0.018 g, 0.01 mmol), aromatic acylchloride (0.140 g, 1 mmol) and benzoxazole (0.119 g, 1 mmol)was heated at 170 C under conventional heating for a few hoursor microwave irradiation of a CEM Discover apparatus for a fewminutes. After completion of reaction, the catalyst was filteredfrom the reaction mixture. The filtrate was diluted with ethyl acetate (50 mL), washed with H2O (3×20 mL), aqueous NaHCO3(2 x20 mL), and dried over Na2SO4. The solvent was removed ina rotary evaporator. The crude product was purified by flash chromatography(90:10 acetone/petroleum ether to give correspondingproduct. The purity and identity of the products were confirmed byGC-MS spectra, which were compared with the spectra in the NISTlibrary, and by 1H and 13C NMR spectroscopy.

17200-30-5, 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.,17200-30-5 ,6-Nitrobenzo[d]oxazole, other downstream synthetic routes, hurry up and to see

Reference：
Article; Nguyen, Linh Ho Thuy; Nguyen, Trang Thi Thu; Tran, Phuong Hoang; Kawazoe, Yoshiyuki; Le, Hung Minh; Doan, Tan Le Hoang; Journal of Catalysis; vol. 374; (2019); p. 110 – 117;,
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.

j00660j To a solution of 6-bromo-2-methylbenzo[djoxazole (0.12 g, 0.55 mmol), compound (R)A-2 (0.10 g, 0.55 mmol), tris(dibenzylideneacetone)dipalladium(0) (51 mg, 0.05 5 mmol) and 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene (64 mg, 0.11 mmol) in dioxane (2 mL) under nitrogen at room temperature was added cesium carbonate (0.36 g, 1.1 mmol). The reaction mixture was stirred at 100 C for 2 hours, then filtered and concentrated in vacuo. The residue was purified by prepHPLC [Instrument: GX-A; Column: Phenomenex Gemini C18 250×50 mm, particle size: 10 tm; Mobile phase: 23-53% acetonitrile in H20 (add 0.05% NH3 H20, v/v)j and lyophilized to give:Compound (R)-51 (27 mg, 16% yield) as a yellow solid: cSFC analytical (R) tR=6.239 mm., purity: 97.35%; LCMS (GG): tRl.664 mm., (ES) m/z (M+H)=3 13.2; ?H-NMR(CD3OD, 400 MHz): 7.89 (d, J=1.6 Hz, 1H), 7.45 (d, J=8.8 Hz, 1H), 7.16 (dd, J18.4 Hz, J22.0 Hz, 1H), 3.34 (s, 1H), 3.16-3.06 (m, 3H), 2.91-2.76 (m, 4H), 2.59 (s, 3H), 2.19-2. 14 (m, 1H), 2.04 (s, 1H), 1.79-1.70 (m, 2H), 1.57-1.53 (m, 1H).

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; FORUM PHARMACEUTICALS, INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; McRINER, Andrew, J.; (267 pag.)WO2017/69980; (2017); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

It is a common heterocyclic compound, the benzoxazole compound, 2-Methylbenzo[d]oxazol-6-amine, cas is 5676-60-8 its synthesis route is as follows.

A slurry of 4-amino-2-methylquinoline (0.158 g) in dichloromethane (10 ml) was added to solution of carbonyl diimidazole (0.162 g) in dichloromethane (5 ml). The mixture was stirred for 2.5 h, solvent removed at reduced pressure and the residue dissolved in dimethylformamide (15 ml). 6-Amino-2-methylbenzoxazole (0.148 g) (Res. Inst. Drugs, Modra, Slovakia. Collect. Czech. Chem. Commun. (1996), 61, 371-380) was added and the mixture warmed to 100 C. for 1 h. Solvent was removed at reduced pressure and triturated with diethyl ether and methanol to give the title compound (0.035 g) as a colourless solid. 1 H NMR delta: 2.59 (3H, s), 2.60 (3H, s), 7.24 (1H, dd, J=1.9, 8.5 Hz), 7.58-7.63 (2H, m), 7.73 (1H, t, J=7.2 Hz),7.89 (1H, d, J=7.7 Hz), 8.06 (1H, d, J=1.8 Hz), 8.13-8.15 (2H, m), 9.22 (1H, brs), 9.55 (1H, brs). m/z (API+): 333 (MH+).

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; SmithKline Beecham p.l.c.; US6699879; (2004); B1;,
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.

Step 2: Bromide 1 (12.8 g, 59.6 mmol) was dissolved in anhydrous THF (220 mL), and the solution was cooled to ?78 C. Solutions of MeMgBr (21.9 mL of a 3.0 M solution in Et2O, 65.6 mmol), sec-BuLi (50.4 mL of a 1.3 M solution in cyclohexane, 65.6 mmol), and 1,4-Cyclohexanedione mono-ethylene ketal (11.2 g, 71.5 mmol) in anhydrous THF (10 mL) were added sequentially at 30-minute intervals. After the final addition, the reaction mixture was allowed to warm to room temperature. The reaction was quenched by the addition of 1N HCl (25 mL). The reaction mixture was diluted with EtOAc (500 mL), washed with saturated NaCl (250 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to provide a mixture of 2 and 3, as a brown oil.

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; Nikam, Sham Shridhar; Scott, Ian Leslie; Sherer, Brian Alan; Wise, Lawrence David; US2003/236252; (2003); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

81282-60-2, 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. 7-Aminobenzo[d]oxazol-2(3H)-one, cas is 81282-60-2,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of 14.9 g N-methyldiethanolamine (3), 44.5 g triethylamine and 120 ml methyl ethyl ketone (MEK) a mixture of 51.6 g methanesulfonic anhydride and 100 ml MEK was dosed at 0 C. Subsequently 14.5 g methanesulfonic acid was dosed at 0 C. After which, 14.5 g 7-amino-2(3H)-benzoxazolone (2) was added and the mixture was heated to reflux followed by a reflux period of 48 hours during which the product crystallized. The product was filtered off after cooling to 0 C. and washed with MEK. The product was dried at 50 C. and 100 mbar to constant weight. The overall yield of this step was about 67% (crude on crude).

The chemical industry reduces the impact on the environment during synthesis,81282-60-2,7-Aminobenzo[d]oxazol-2(3H)-one,I believe this compound will play a more active role in future production and life.

Reference：
Patent; Rheenen, Jeroen Van; Muijselaar, Wilhelmus G.H.M.; Teunissen, Hendrik; US2011/86862; (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 13: 2-oxo-2,3-dihydrobenzo[d]oxazole-6-carbonitrile To a solution of 6-bromo benzoxazolinone (2 g, 9.4 mmol) in DMF (20 mL) was added CuCN (16.79 g, 188 mmol), and the reaction was stirred at 175 C. for 6 h. The reaction progress was monitored by TLC (100% EtOAc). The reaction was diluted with EtOAc (10 mL) and filtered through Celite brand filter agent. The organic layer was concentrated and purified by column chromatography (silica gel, 0-50% EtOAc in hexanes) to give the title compound. MS (ESI pos. ion) m/z: 158.9 (MH-).

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; AMGEN INC.; BISWAS, Kaustav; CHEN, Jian J.; GORE, Vijay Keshav; HARRIED, Scott; HORNE, Daniel B.; KALLER, Matthew R.; MA, Vu Van; SHAM, Kelvin; ZHONG, Wenge; US2014/45855; (2014); 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.

NaH (280 mg, 7.00 mmol) was added to a chilled (0 0C) solution of benzo[d]oxazol-2(3H)- one (650 mg, 4.81 mmol) in tetrahydrofuran (20 mL). After 0.5 hours, methyl iodide (1.03 g, 7.25 mmol) was added dropwise with stirring, maintaining a temperature of 0 0C. The resulting solution was then stirred for 6 hours at room temperature. The reaction mixture was then quenched by the addition of ethanol (10 mL), and the mixture was concentrated. Water (50 mL) was then added and the resulting solution was extracted with dichloromethane (3 x 20 mL). The organic layers were combined, dried (Na2SO4), filtered and concentrated to afford 0.62 g (82%) of 3-methylbenzo [d] oxazol-2 (3H)-one as a light red solid.

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; MEMORY PHARMACEUTICALS CORPORATION; WO2007/98418; (2007); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

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

To a colorless solution ofbenzo[d]oxazol-2-amine(200 mg, 1.491 mmol) in DMF (10 ml) was added sodiumhydroxide (20N, 149 mul., 2.98 mmol), to give a green suspension.The mixture was stirred for 15 min at room temperature.Carbon disulfide (225 ul., 3.73 mmol) was added to give adark brown solution. The reaction was stirred for 15 min atroom temperature, followed by the addition of sodiumhydroxide (20N, 149 ul., 2.98 mmol) and stirred for an additional 10 min. Iodomethane (224 mul., 3.58 mmol) was then added dropwise. A green solid precipitated after 12 min. Thereaction stirred for a further 2 hr. The solid was collected byfiltration, washed with DMF (2xl ml), H20 (2xl ml), driedunder the house vacuum for 30 min and further dried in anoven in vacuo over night to afford the expected product,dimethyl benzold]oxazol-2-ylcarbonimidodithioate (258.5mg, 1.085 mmol, 72.7percent yield), as a white solid

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; BRISTOL-MYERS SQUIBB COMPANY; COOK II, JAMES H; MCDONALD, IVAR M; KING, DALTON; OLSON, RICHARD E; WANG, NENGHUI; IWUAGWU, CHRISTIANA I; ZUSI, F.CHRISTOPHER; MACOR, JOHN E; (330 pag.)JP5714745; (2015); B2;,
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.

Step: 23bSynthesis of 5-Amino-3H-benzooxazol-2-Procedure:Pd-c (1 1 lmg) was added to a stirred solution of 5-Nitro-3H-benzooxazol-2-one (1.1 1 lg, 6.168mmol) was dissolved in Methanol (20ml) and THF (10ml). The contents were hydrogenated with stirring for 6 hrs. The reaction was monitored by the TLC (10% CHC13: MeOH). The resulting reaction mixture was filtered through celite, concentrated and washed with hexane. The solid obtained was dried under reduced pressure to afford 930mg (100% yield) of 5-Amino-3H-benzooxazol-2-one.

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; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; SENGUPTA, Saumitra; RAJAGOPALAN, Srinivasan; BELAVAGI, Ningaraddi; RAMACHANDRA, Muralidhara; WO2012/59932; (2012); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem