Dimethylformamide → 4-[(3-Chloropropyl)sulfanyl]-2-nitroaniline

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Reaction Steps

6 G. of 2-nitro-4-thiocyanatoaniline in 30 ml. of dimethylformamide is treated under nitrogen with 1.2 g. of sodium borohydride at 20° to 30°. After 11/2 hours 15 ml. of acetone is added, followed 2 hours later by 10 g. of 3-chloropropylbromide. The mixture is left at 20°-25° for 16 hours, then diluted with water. The oily product is extracted into chloroform and passed through a silica column. 2-Nitro-4-(3-chloropropylthio)aniline is isolated by evaporation of the solvent.

Provenance & Evidence