Water → HCID 117974116, compound

Participants

Reaction Steps

0.06 g of sodium hydride (60%) was added to 5 ml of a solution of 0.53 g of 2-(3-bromothiophen-2-yl)-5-pentafluoroethylbenzoxazole and 0.1 ml of ethanethiol in NMP at 0° C., and the mixture was stirred at room temperature for 1 hour. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with a 10% aqueous hydrochloric acid solution and a saturated aqueous salt solution, and dried over anhydrous sodium sulfate, then concentrated under reduced pressure. To a mixture of the residue and 5 ml of chloroform was added 0.66 g of 3-chloroperoxybenzoic acid (purity of 65% or more), under ice cooling, and the mixture was stirred at room temperature for 1 hour. A 10% aqueous sodium thiosulfate solution was poured into the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with a saturated aqueous sodium bicarbonate solution and dried over anhydrous sodium sulfate, then concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 0.32 g of 2-(3-ethylsulfonylthiophen-2-yl)-5-pentafluoroethylbenzoxazole (Compound of Present Invention (35)).

Provenance & Evidence