Synthesis and x-ray crystallographic study of n,n’-bis(2-, 3-, and 4-methoxybenzamidothiocarbonyl) hydrazines

Abstract

Introduction: Most of carbonyl thioureas have been synthesized from the reaction of carbonyl isothiocyanate with amine compound in acetone. Only a few of them have been synthesized from diamine compound to produced bis-carbonyl thioureas. Objective: To investigate the one-pot reaction of 2, 3, and 4-methoxybenzoyl chloride with ammonium thiocyanate and hydra-zine in acetone by reflux condition. Methods: Each of the crystal compounds was analysed by X-ray crystallography. Result: Three compound of bis-thiorea derivatives, namely N, N’-bis (2-methoxy-benzamidothiocarbonyl) hydrazine (1), N, N’-bis (3-methoxybenzamidothiocarbonyl)-hydrazine (2), and N, N’-bis (4-methoxybenzamidothiocarbonyl) hydrazine (3) were successfully synthesised by the reaction of each 2, 3, and 4-methoxybenzoyl chloride with ammonium thiocyanate and hydra-zine in acetone. The structure of these compounds was studied by chemical crystallography. Conclusion: Compound 1 and 3 were crystallized in the triclinic crystal system while compound 2 was crystallized in the mono-clinic crystal system. The thiourea moiety in all compounds have trans geometry and each of the hydrogens of the amide group is trans to the carbonyl group.