Dimethylformamide → 2-Nitro-4-[(prop-2-yn-1-yl)sulfanyl]aniline

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Reaction Steps

5.85 G. of 1-amino-2-nitro-4-thiocyanatobenzene in 20 ml. dimethylformamide is treated under nitrogen with 1.14 g. sodium borohydride at not greater than 30° C. The mixture is stirred for 1 hour at 15°-20° C, then treated with 5 ml. of propargyl bromide at 20°-25° C. After a further three hours, water is added and the crude product extracted with chloroform. The dried chloroform solution is passed through a column of silica gel to remove a litte polar material. Pure 1-amino-2-nitro-4-(prop-2-yn-1-ylthio)benzene is obtained from the eluate.

Provenance & Evidence