Molbank, Vol. 2019, Article M1052: 1-[N-Methyl-N-(Phenyl)amino]-3-(4-Methylphenyl)Thiourea (Molbank)

The title compound, 1-[N-methyl-N-(phenyl)amino]-3-(4-methylphenyl)thiourea (1), was synthesized by the reaction of 1-methyl-1-phenyl hydrazine and 4-tolyl isothiocyanate, and was characterized by spectroscopy (1H and 13C{1H} NMR, IR, and UV), elemental analysis as well as by single crystal X-ray crystallography. In the solid state, the molecule exists as the thioamide tautomer and features an anti-disposition of the thioamide-N-H atoms; an intramolecular N-H···N hydrogen bond is noted. The molecular conformation resembles that of the letter L. In the molecular packing, thioamide-N1-H···S1(thione) hydrogen bonds lead to centrosymmetric eight-membered {···HNCS}2 synthons. The dimers are assembled into a supramolecular layer in the bc-plane by phenyl- and methyl-C-H···?(phenyl) interactions.