Sodium Hydroxide → HCID 9904156, compound

Participants

Reaction Steps

To a solution of tert-butyl hydrazine hydrochloride (523 mg, 3.50 mmol) in ethyl alcohol (20 ml) was added powdered sodium hydroxide (168 mg, 4.20 mmol), followed by 3-(4-chlorophenyl)-2-cyano-3-methylthioacrylamide (884 mg, 3.50 mmol) and the mixture was heated at reflux for 4 h. On cooling, the solvent was removed under reduced pressure and the residue partitioned between water (80 ml) and ethyl acetate (80 ml). The aqueous layer was further extracted with ethyl acetate (2×80 ml) and the combined organic layers were washed with brine (1×100 ml), dried (MgSO4) and concentrated under reduced pressure. The residue was subjected to column chromatography (SiO2, 45-75% ethyl acetate-hexane) to afford the title compound (780 mg) after recrystallisation from methanol as a colorless solid m.p. 156°. δH (d6DMSO) 1.66 (9H, s), 5.16 (2H, br s), 5.68 (2H, br s), 7.42 (2H, dt, J 8.6, 2.1 Hz), and 7.51 (2H, dt, J 8.7, 2.1 Hz).

Provenance & Evidence