Synthesis, spectral characteristics and molecular structure of N-(2,2,2-trichloro-1-(hydrazinecarbothioamido)ethyl)carboxamides

Abstract

Thiosemicarbazide derivatives are widely used as substrates for organic synthesis, and as analytical reagents and have a wide range of biological activities. In this work, we report synthesizing a series of new thiosemicarbazide derivatives functionalized with an N-(2,2,2-trichloroethyl)carboxamide group at the thioamide nitrogen atom. These compounds were obtained by adding hydrazine hydrate to N-(2,2,2-trichloro-1-isothiocyanatoethyl)carboxamides. Optimization of reaction conditions was carried out under the control of LC-MS analysis. The highest yields were observed at room temperature using MTBE as a solvent. The yield of target products under these conditions was 68–94 %. The structure of the obtained compounds was confirmed by 1H, 13C NMR, and IR spectroscopy data, as well as the selective X-ray diffraction analysis carried out for 3-methyl-N-(2,2,2-trichloro-1-(hydrazinecarbothioamido)ethyl)butanamide.