Methoxycarbonyl isothiocyanate → 1-(3-Methoxycarbonyl-2-thioureido)-2-nitro-4-methoxymethylthiobenzene

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Reaction Steps

1 G. of 1-amino-2-nitro-4-methoxymethylthiobenzene, prepared according to Example VIII, in 50 ml. acetone is treated with 3 g. methoxy carbonyl isothiocyanate at room temperature for several days. The solution is concentrated and the residue triturated with methanol and recrystallized from acetone to afford 1-(3-methoxycarbonyl-2-thioureido)-2-nitro-4-methoxymethylthiobenzene. This latter compound is treated for four hours in a refluxing mixture of 160 ml. methanol and 40 ml. water with 4 g. iron powder (added in two portions) and 1 g. ferrous sulfate. The mixture is filtered, and the filtrate concentrated. The residue is dissolved in chloroform, washed with water, then the solvent is evaporated to afford 2-amino-1-(3-methoxycarbonyl-2-thioureido)-4-methoxymethylthiobenzene.

Provenance & Evidence