Hydrogen Sulfide → 3-Amino-2-cyano-3-(dipropylamino)propenethioamide

Participants

Reaction Steps

An attempt at conversion by the method of Example IV, part D, was unsuccessful. Thus a mixture of 28 g of 3-amino-2-cyano-3-(dipropylamino)propenenitrile, 14.7 g of triethylamine and 100 ml of pyridine in a pressure bottle was cooled to -70° and 10 g of hydrogen sulfide were added. The bottle was capped and allowed to stand at ambient temperature during two days, then heated at 80° for about 16 hours. The mixture was concentrated under reduced pressure and the residue was dissolved in a minimum of toluene containing a trace of ethanol. The solid which separated on cooling was collected to obtain 9.6 g of 3-amino-2-cyano-3-(dipropylamino)propenethioamide, m.p. 141°-144°. The nmr spectrum was consistent with the assigned structure.

Provenance & Evidence