Synthesis and spectral characteristics of N-(2,2,2-trichloro-1-((5-(methylthio)-1,3,4-thiadiazol-2-yl)amino)ethyl)carboxamides
DOI:
https://doi.org/10.17721/fujcV13I2P51-57Keywords:
synthesis, 1,3,4-thiadiazole, dithiobiurea, carboxamide, alkylationAbstract
In this work, we present the synthesis of a new series of 5-amino-1,3,4-thiadiazole-2-thiols containing a pharmacophore alkylamide fragment. The synthesis involved reacting the starting N-(2,2,2-trichloro-1-(2-(phenylcarbamothioyl)hydrazine-1-carbothioamido)ethyl)carboxamides with methyl iodide in ethanol under heating. The reaction proceeded through an N,S-alkylation step, followed by cyclization, which formed the thiadiazole ring. Yields ranged from 58% to 67%. The structures of the obtained compounds were confidently confirmed by spectral methods. The 1H NMR spectra displayed clear signals for two NH protons (9.69-9.09 and 8.75-8.54 ppm), the methine proton of the alkylamide fragment (6.89-6.72 ppm), and the methylthiol group (2.64-2.62 ppm). In 13C NMR spectra, characteristic signals included the carbon of the carboxamide group (169.0-166.5 ppm), the C=N atoms of the thiadiazole ring (166.5-155.1 ppm), the carbon of the CCl3 group (101.0-100.7 ppm), the methine atom of the alkylamide fragment (70.3-69.9 ppm), and the methylthiol carbon (16.4 ppm).
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