Ethyl 3-[2-(p-tolylcarbamothioyl)hydrazinylidene]butanoate

Abstract

The title compound, C14H19N3O2S, was obtained from a condensation reaction of N-(p-tolyl)hydrazinecarbothioamide and ethyl acetoacetate. The molecule assumes an E configuration; the thiosemicarbazide and ester groups are located on the opposite sides of the C=N bond. The almost planar thiosemicarbazide unit (r.m.s. deviation = 0.0130 Å) is tilted at a dihedral angle of 49.54 (12)° with respect to the benzene ring. Intermolecular N—H...N and N—H...S hydrogen bonding stabilizes the crystal structure. The ethoxy group of the ester unit is disordered over two positions, with a site-occupancy ratio of 0.680 (10):0.320 (10).