Benzaldehyde → 2-amino-4-phenyl-6-sulfanylidene-1H-pyridine-3,5-dicarbonitrile

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Reaction Steps

Following the method of Elghandour et al. (Ind. J Chem. 1997, B36, 79), a stirred solution of 0.66 g (10 mmol) malonitrile, 1.0 g (10 mmol) cyanothioacetamide, 1.0 ml (10 mmol) benzaldehyde and 0.1 ml (1.0 mmol) piperidine in 50 ml ethanol was heated at reflux for 1.5 hours. The reaction mixture was then poured onto ice-water and acidified to pH 3 with 1M hydrochloric acid. The resulting crystals were collected by filtration. Chromatography (ethyl acetate) afforded 0.24 g (10%) 6-amino-4-phenyl-2-thioxo-1,2-dihydro-pyridine-3,5-dicarbonitrile as a yellow crystalline solid. EI-MS m/e (%): 252 (M+, 100), 251 ([M—H]+, 92).

Provenance & Evidence