Dimethylformamide → 2-Nitro-4-[(pyridin-2-yl)sulfanyl]aniline

Participants

Reaction Conditions

Reaction Steps

A solution of 5.85 g. of 1-acetamido-2-nitro-4-thiocyanatobenzene in 20 ml. dimethylformamide is cooled, under nitrogen, to about 0°C. and 1.14 g. of sodium borohydride is added. The exothermic reaction is controlled to less than about 30°C., then the mixture is stirred for 1 hour at 20°-30°C. 6 Ml. of 2-bromopyridine is added and the mixture warmed slowly to about 110°C. and kept at that temperature for 1 hour. The mixture is cooled, diluted with water, and filtered. The crude product is recrystallized from aqueous methanol, yielding 1-amino-2-nitro-4-(pyrid-2-ylthio)benzene.

Provenance & Evidence