Dimethylformamide → N-{2-Nitro-4-[(pyrazin-2-yl)sulfanyl]phenyl}acetamide

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Reaction Steps

A solution of 9.6 g. 1-acetamido-2-nitro-4-thiocyanatobenzene in 60 ml. dimethylformamide is treated under nitrogen with 1.52 g. of sodium borohydride, the exothermic reaction being controlled so that the temperature does not exceed 30°C. After stirring the mixture at 20°-25°C. for 1 hour, 15 ml. of acetone is added, then, after 2 hours, 9.1 g. of 2-chloropyrazine is added. The mixture is warmed slowly and kept at 100°-110°C. for 3 hours, cooled and diluted with water. The product is filtered off and washed with water, pentane and recrystallized from methanol affording 1-acetamido-2-nitro-4-(pyrazin-2-ylthio)benzene.

Provenance & Evidence