Sodium methanethiolate → 5-Methoxy-3-(methylthio)benzo[b]thiophene-2-carboxamide

Participants

Reaction Steps

Sodium thiomethoxide (93 mg, 1.32 mmol) is added to a suspension of 3-chloro-5-methoxybenzo[b]thiophene-2-carboxamide (250 mg, 1.03 mmol) in 2 mL of DMF. After 1 hour, an additional amount of sodium thiomethoxide (13 mg) is added. The reaction mixture is diluted with ethyl acetate and washed with 1N NaOH, 1N HCl, water, and brine. The organic layer is dried over MgSO4. Filtration followed by concentration in vacuo and recrystallization from ethyl acetate:hexane gives 5-methoxy-3-(methylthio)benzo[b]thiophene-2-carboxamide in 72% yield; mp=171°-173° C.

Provenance & Evidence