Malononitrile → HCID 9880202, compound

Participants

Reaction Steps

2-Imino-3-cyano-7-methoxy-4-(3′-phenyl)-2H-thiochromene: To a mixture of (2-mercapto-4-methoxyphenyl)-(3′-methoxyphenyl)-methanone (35 mg, 0.13 mmol) and malononitrile (8.5 mg, 0.13 mmol) in 200 μL of dry ethanol was added piperidine (7.0 μL, 0.06 mmol) at 0° C. The resultant mixture was stirred at 0° C. for 2.5 h. The solvent was evaporated and the residue was purified by flash chromatography (25% ethyl acetate/hexanes) to yield 31 mg (75%) of 2-imino-3-cyano-7-methoxy-4-(3′-methoxy-phenyl)-2H-thiochromene as an orange waxy oil. 1H NMR (CDCl3): 9.31 (brs, 1H), 7.42–7.46 (m, 1H), 7.03–7.11 (m, 2H), 6.91 (d, J=7.8 Hz, 1H), 6.85–6.86 (m, 1H), 6.80 (brs, 1H), 6.68 (dd, J=9.1 and 2.6 Hz, 1H), 3.85 (s, 3H), 3.84 (s, 3H).

Provenance & Evidence