[NH2:1][C:2]([O:8][CH2:9][CH2:10][CH3:11])=[C:3]([C:6]#[N:7])[C:4]#[N:5].C(N(CC)CC)C.[SH2:19]>N1C=CC=CC=1.O>[NH2:1][C:2]([O:8][CH2:9][CH2:10][CH3:11])=[C:3]([C:4]#[N:5])[C:6](=[S:19])[NH2:7]A stirred mixture of 141 g of 3-amino-2-cyano-3-propoxypropenenitrile and 94.4 g of triethylamine in 250 ml of pyridine was heated at 80° for 4 hours while hydrogen sulfide gas was continually passed through the mixture. Thin-layer chromatography indicated reaction to be complete. The reaction mixture was diluted to 2 liters with water and the pale yellow precipitate was collected by filtration. The precipitate was recrystallized from ethanol to give 114 g of 3-amino-2-cyano-3-propoxypropenethioamide, m.p. 174°.
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