Acetonitrile → N-Methyl-N'-[2-[[3-(N,N-dimethylaminomethyl)phenyl]methylthio]ethyl]-2-nitro-1,1-ethenediamine

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Reaction Steps

2-[[3-(N,N-Dimethylaminomethyl)phenyl]methylthio]ethanamine (3 g) and 1-nitro-2,2-bis(methylthio)ethylene (2.2 g) were heated under reflux in acetonitrile for 7 hours. The solvent was removed and the residual oil used without further purification. The oil was treated with ethanolic methylamine (33%, 34 ml) and heated under reflux for 3 hours. The solvent was removed and the residual oil was purified by column chromatography on silica with methanol. The resultant orange oil was triturated with ether to give the title compound as a white crystalline solid (0.23 g) m.p. 62°-4°. TLC silica; ethyl acetate:isopropanol:water:0.88 ammonia (25:15:8:2) Rf 0.36.

Provenance & Evidence