m-Chloroperbenzoic acid → HCID 59296139, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 200 mg of 4-[4-butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethylsulfanyl]-benzonitrile (prepared according to the method described in example 14) in 4 ml of dichloromethane at 0° C. was added 80 mg of meta-chloroperbenzoic acid. The resulting mixture was stirred at 0° C. for 5 hours, at room temperature for 2 hours than kept in the fridge overnight. A saturated aqueous solution of sodium hydrogenocarbonate was added and the organic layer was separated. The aqueous layer was extracted with dichloromethane. The combined extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (gradient of 1 to 4% acetone/dichloromethane) to give 185 mg of 4-[4-butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethylsulfinyl]-benzonitrile, which was transformed into 3-{4-[4-butyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethanesulfinyl]-phenyl}-4H-[1,2,4]oxadiazol-5-one according to the method described in example 1.

Provenance & Evidence