Hydrogen Sulfide → HCID 85942025, compound

Participants

Reaction Steps

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.

Provenance & Evidence