Ethyl chloroacetate → 3-(3-Benzyl-4-oxothiazolidin-2-ylideneamino)-4-ethylaminobenzonitrile

Participants

Reaction Conditions

Reaction Steps

To a 100 mL flask was added 1-benzyl-3-(5-cyano-2-ethylaminophenyl)thiourea (1.0 g, 3.2 mmol), anhydrous ethanol (40 mL), ethyl chloroacetate (0.39 g, 3.2 mmol) and then DBU (0.58 g, 3.8 mmol). The reaction was heated at 80° C. for 30 min. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure and chromatographed (silica gel, 1:1 EtOAc/Hex) to afford the title product (0.98 g, 87%). 1H-NMR (CDCl3): δ 7.38 (6H, m), 7.11 (1H, d), 6.50 (1H, d), 5.05 (2H, s), 3.96 (2H, s), 3.01 (2H, m), 1.03 (3H, t).

Provenance & Evidence