[NH2:1][C:2]([N:8]([CH2:11][CH3:12])[CH2:9][CH3:10])=[C:3]([C:6]#[N:7])[C:4]#[N:5].C(N(CC)CC)C.N1C=CC=CC=1.[SH2:26]>CN(C)C=O>[NH2:1][C:2]([N:8]([CH2:9][CH3:10])[CH2:11][CH3:12])=[C:3]([C:4]#[N:5])[C:6](=[S:26])[NH2:7]A mixture of 72.6 g of 3-amino-2-cyano-3-(diethylamino)propenenitrile, 44.7 g of triethylamine, 200 ml of pyridine, and 50 ml of dimethylformamide was saturated at 60° with hydrogen sulfide. The temperature was increased to 75° while hydrogen sulfide was passed through the solution. After heating at 75° for 2 hours, thin-layer chromatographic analysis indicated the reaction was incomplete. After about 60 hours at room temperature the mixture was heated at 75° for an additional 4 hours. The mixture was allowed to cool to ambient temperature, then was poured into 1750 ml of ice-water mixture. The cold slurry was stirred for 1 hour and the solid was isolated by filtration. The solid was washed with ice-water and recrystallized from 250 ml of ethanol to give 56 g of 3-amino-2-cyano-3-(diethylamino)propenethioamide, m.p. 151°-152°. The nmr spectrum was consistent with the assigned structure.
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