Day: May 18, 2021

13673-62-6, 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. 2-(Methylthio)benzo[d]oxazole, cas is 13673-62-6,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

In order to prepare intermediate c-3, chlorosulfonic acid (3890 g; 33.3 mol) was stirred under nitrogen. Then intermediate c-2 (1288 g; 7.80 mol) was added portionwise maintaining the internal temperature below 60C by external cooling. After complete addition of intermediate b-2 the reaction mixture was stirred overnight at 85C. The heating was removed and the reaction mixture was cooled down until 65C. SOC12 was added dropwise while maintaining a controlled release of gases by good stirring. This mixture was stirred overnight at 65C. This reaction mixture was added to a well stirred mixture of EtOAc (6.9 kg) and ice (9.2kg) while maintained the temperature below 0C. The organic layer was isolated. The aqueous phase was extracted with EtOAc (3.1 KG). The combined organic layer was washed with 7.5 % NAHC03 (210 g/2.8 L water). Because the pH of this water layer was still 1, therefore another 125 g NAHC03 was added. This mixture was stirred for 1 hour, then the phases were separated. The organic layer was dried with NA2C03 (2.5 kg). After filtration 1935 g of intermediate c-3 was obtained (yield 94%, HPLC purity 94%) and used in the preparation of compound c-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 2-(Methylthio)benzo[d]oxazole, 13673-62-6

Reference：
Patent; TIBOTEC PHARMACEUTICALS LTD.; WO2005/30739; (2005); 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.

Preparation of 1-(4-(trifluoromethyl)benzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-7-yl)urea Commercially available 4-trifluoromethylbenzylamine (1 ml, 7 mmol) was dissolved in 20 ml of AcOEt and at 0C triphosgene (2 g, 7 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound 1c (700 mg, 4.66 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt 4 / petroleum ether 6). 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 320 mg of a white solid. Yield = 19.5% 1HNMR (DMSO, 400 MHz) delta 4.41 (2H, d, J = 6 Hz), 6.67 (1H, dd, J = 7.6 Hz, J’ = 1.2 Hz), 7.00 (1H, t, J = 8 Hz), 7.09 (1H, t), 7.51 (2H, d, J = 8 Hz), 7.70 (3H, m), 8.73 (1H, s), 10.60 (1H, bs); [M+1] 352.1 (C16H12F3N3O3 requires 351.3).

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 7-Aminobenzo[d]oxazol-2(3H)-one, 81282-60-2

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

22876-19-3, 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. 5-Chlorobenzo[d]oxazole-2(3H)-thione, cas is 22876-19-3,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

Subsequently, 5-chloro-2-mercaptobenzoxazole (3.1 g, 16.7 mmol) was dissolved in thionyl chloride (30 mL, 413 mmol). DMF (1.5 mL) was added and the reaction mixture was heated at 65 C. for 45 min. The solvent was removed under reduced pressure and to the residue was added toluene (2*60 mL) followed by evaporation each time to remove the excess SOCl2 (azetrope). The resultant crude product was dissolved in ethyl acetate (100 mL), washed with water (100 mL) and dried over Na2SO4. Evaporation of ethyl acetate gave 2,5-dichlorobenzoxazole, compound 19, as a red oil (3.2 g).

The chemical industry reduces the impact on the environment during synthesis,22876-19-3,5-Chlorobenzo[d]oxazole-2(3H)-thione,I believe this compound will play a more active role in future production and life.

Reference：
Patent; GALLEON PHARMACEUTICALS, INC.; US2011/224269; (2011); A1;,
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.

General procedure: Commercially available 5-chloro-2-mercapto benzoxazole or benzothiazole (10 mmol) and K2CO3 (15mmol) were added to 50 mL of acetone. After 10 min, appropriate 1-bromo–bromoalkane (12 mmol) was added and the mixture was stirred at room temperature for 24 h. After this time the suspension was filtered from inorganic material and the solvent was evaporated under reduced pressure. The residue was suspended in water and extracted with diethyl ether (3 × 50 mL). The combined extracts were washed with water, dried over anhydrous Na2SO4, and evaporated under reduced pressure to givein termediates 9-12 that were used without further purification for the final step. For analytical purpose,a little amount was purified by means of flash chromatography, using cyclohexane/ethyl acetate 9.5:0.5v/v as eluent. Analytical and spectral data are reported for novel compounds 9-12

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; Romeo, Giuseppe; Prezzavento, Orazio; Intagliata, Sebastiano; Pittala, Valeria; Modica, Maria N.; Marrazzo, Agostino; Turnaturi, Rita; Parenti, Carmela; Chiechio, Santina; Arena, Emanuela; Campisi, Agata; Sposito, Giovanni; Salerno, Loredana; European Journal of Medicinal Chemistry; vol. 174; (2019); p. 226 – 235;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

54903-16-1, 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-Oxo-2,3-dihydrobenzo[d]oxazole-6-carboxylic acid, cas is 54903-16-1,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

c) Synthesis of compound (I-66) [Show Image] A compound 19 trihydrochloride (0.49 g, 1.40 mmol), and the known (J. Chem. Soc., 1921, viol.119, pp.1425-1432) compound 20 (0.25 g, 1.40 mmol) were dissolved in DMF (10 ml), HOBt monohydrate (0.21 g, 1.50 mmol), DMAP (17 mg, 0.14 mmol), N-methylmorpholine (0.69 ml, 6.30 mmol), and EDC (0.30 g, 1.50 mmol) were added, and the mixture was stirred at room temperature for 3 hours. Water (50 ml) was added, and the precipitated crystal was filtered, washed with water, and then dried. The resulting solid was recrystallized from ethyl acetate-methanol-diethyl ether to obtain a compound (I-66) (0.50 g, yield 89%). mp 156-158C 1H-NMR (DMSO-d6 / TMS) deltappm: 2.48-2.64 (m, 6H), 3.10-3.20 (m, 4H), 3.42 (q, J = 6.3Hz, 2H), 6.94 (d, J = 9.1Hz, 2H), 7.15 (d, J = 8.1Hz, 1H), 7.22 (d, J = 9.1Hz, 2H), 7.69-7.75 (m, 2H), 8.04 (t, J = 6.3Hz, 1H).

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-Oxo-2,3-dihydrobenzo[d]oxazole-6-carboxylic acid, 54903-16-1

Reference：
Patent; Shionogi&Co., Ltd.; EP2184272; (2010); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

Name is 2-Oxo-2,3-dihydrobenzo[d]oxazole-6-carboxylic acid, as a common heterocyclic compound, it belongs to benzoxazole compound, and cas is 54903-16-1, its synthesis route is as follows.

i. 2-oxo-2,3-dihydro-benzooxazole-6-carbonic-acid 13 (38.6 mg, 0.22 mmol), intermediate 12 (95.5 mg, 0.22 mmol) and 4-methylmorpholine (0.72 mL, 0.66 mmol) were given to DMF (3 mL). N-(3-dimethylaminopropyl)-N’- ethylcarbodiimide hydrochloride (41.4 mg, 0.22 mmol) and 1- hydroxybenzotriazolehydrate (29,2 mg, 0.2 mmol) were added at RT. It was stirred for 15 h at RT. The reaction mixture was poured onto water and extracted twice with ethyl acetate. The pooled organic phases were dried over sodium sulphate, filtrated and concentrated in vacuo until dryness. The oily residue was comminuted with diethyl ether, and the emerging solid was filtered off. A colourless solid (14, 50.4 mg, 0.09 mmol, 44%) in high purity was yielded.

54903-16-1, 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.,54903-16-1 ,2-Oxo-2,3-dihydrobenzo[d]oxazole-6-carboxylic acid, other downstream synthetic routes, hurry up and to see

Reference：
Patent; MERCK PATENT GMBH; SCHIEMANN, Kai; SCHULTZ, Melanie; STAEHLE, Wolfgang; WO2010/115491; (2010); A2;,
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.

General procedure: The SBOs were prepared by the base-catalysed condensation of the appropriate 5-halogeno-2-methylbenzoxazole with the requisite aromatic aldehyde under phase transfer conditions. In a typical experiment, equimolar quantities (5 mmol) of the starting materials were dissolved in dichloromethane (20-50 ml) in the presence of benzyltriethylammonium chloride (3 mmol) and stirred magnetically under a nitrogen atmosphere as an aqueous solution of sodium hydroxide (50%, w/v, 5 ml) was added dropwise over a period of 10 min. After being stirred for 2-36 h until analytical thin layer chromatography indicated that the reaction was complete, the mixture was diluted with water (50 ml) and the SBO was extracted with dichloromethane (3×20 ml), dried (MgSO4), filtered, evaporated under reduced pressure and recrystallized from aqueous methanol or ethanol.

The chemical industry reduces the impact on the environment during synthesis,701-16-6,5-Fluoro-2-methylbenzo[d]oxazole,I believe this compound will play a more active role in future production and life.

Reference：
Article; Ayrton, Stephen T.; Panova, Jekaterina; Michalik, Adam R.; Martin, William H.C.; Gallagher, Richard T.; Bowen, Richard D.; International Journal of Mass Spectrometry; vol. 345-347; (2013); p. 120 – 131;,
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.

2j: 3-(3-Chloro-propyl)-3H-benzoxazol-2-one Sodium hydride (60% in oil dispersion) (155 mmol) was washed with diethyl ether under an argon atmosphere, then suspended in DMF (75 mL). 3H-Benzoxazol-2-one (148 mmol) was dissolved in DMF (150 mL) and added drop wise to the slurry. After stirring for ca. 30 min. the mixture was homogenous and was then cooled to -5 C on an acetone-ice bath. 1-Bromo- 3-chloropropane (296 mmol) was dissolved in DMF (50 mL) and added drop wise to the cold solution. The reaction mixture was allowed to come to room temperature and stirring was continued for 18h. Poured into H2O, the aqueous phase was extracted x3 with ethyl acetate.The combined organic fractions were washed x2 with NH4Cl (aq., sat.) dried on MgSO4 and the solvent was removed by evaporation to yield an oil which solidified on standing. The obtained solid was washed with diethyl ether and dried in vacuo. The product was udes without further purification.Yield = 54%1H NMR (D6-DMSO): 2.16 (qui, 2H); 3.71 (t, 2H); 3.96 (t, 2H); 7.14 (t, IH); 7.24 (t, IH);7.29-7.36 (2H).

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; H. LUNDBECK A/S; WO2009/106534; (2009); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

3621-81-6, 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. 2,5-Dichlorobenzooxazole, cas is 3621-81-6,the benzoxazole compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2,5-dichlorobenzo[d]oxazole (5 g, 26.6 mmol) in dry dichloromethane (50 ml_) was added 2M dimethylamine in THF (26.6 mL, 53.2 mmol), and the mixture was cooled to 0C. To this cold reaction mixture was added triethylamine (5.6 mL, 39.9 mmol) drop-wise and the mixture was allowed to stir at room temperature for 4 h. After the completion of the reaction, the reaction mixture was treated with H20 (2 x 20 mL) and extracted with dichloromethane. The organic layer was separated, dried over Na2S04, filtered and evaporated to afford a white solid which was triturated with diethyl ether to afford the titlecompound (4.9 g, 94 %). (0493) MS: 197.2 (M+H)+. (0494) 1H-NMR (400 MHz, DMSO-c/6) d = 7.40 (d, J = 8.40 Hz, 1 H), 7.30 (d, J = 2.00 Hz, 1 H), 6.99- 6.99 (m, 1 H), 3.13 (s, 6H).

The chemical industry reduces the impact on the environment during synthesis,3621-81-6,2,5-Dichlorobenzooxazole,I believe this compound will play a more active role in future production and life.

Reference：
Patent; AC IMMUNE SA; NAMPALLY, Sreenivasachary; GABELLIERI, Emanuele; MOLETTE, Jerome; (220 pag.)WO2019/134978; (2019); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem

Name is 2-Chloro-6-fluorobenzo[d]oxazole, as a common heterocyclic compound, it belongs to benzoxazole compound, and cas is 153403-53-3, its synthesis route is as follows.

Amine hydrochloride (737.4 g, 2.59 mol) and 2-chloro-5-fluorobenzoxazole (457.4 g, 2.67 mol) were suspended in N,N-dimethylformamide (3.69 L). Triethylamine (2.17 L, 15.54 mol) and potassium iodide (128.9 g, 0.78 mol) were added thereto. To the mixture, 2-chloro-5-fluorobenzoxazole (457.4 g, 2.67 mol) dissolved in N,N-dimethylformamide (1.48 L) was added dropwise under ice-cooling and stirring. After finishing the drop-wise addition, the mixture was stirred under ice-cooling for 1 hour, at room temperature for 1 hour and then at 40 C. for 2 hours. The mixture was cooled to room temperature under ice-cooling. Water (5.16 L) was added dropwise and the mixture was suspended. After stirring at room temperature for 3 hours, the precipitated crystals were filtrated and washed with water (5.16 L) to give the desired crude product (903.4 g).

153403-53-3, 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.,153403-53-3 ,2-Chloro-6-fluorobenzo[d]oxazole, other downstream synthetic routes, hurry up and to see

Reference：
Patent; Shionogi & Co., Ltd.; US2010/273841; (2010); A1;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem