1,3-Thiazole derivatives are of considerable interest in pharmacy, medicine, and agriculture as potential biologically active compounds. In this work, we report for the first time a convenient and efficient method for the synthesis of N-amidoalkylated derivatives of 2-amino-1,3-thiazole. The starting N-(2,2,2-trichloro-1-thioureidoethyl)carboxamides readily react with α-bromoacetophenone in ethanol at 20 °C in the presence of equimolar triethylamine, which serves to neutralize the released hydrogen bromide. Under these conditions, the desired N-amidoalkylated 1,3-thiazole derivatives were obtained in 68–75 % yields. Attempts to perform the counter-synthesis by direct amidoalkylation of 4-phenylthiazol-2-amine resulted in severe tarring of the reaction mass and did not lead to product isolation. The structures of the synthesized compounds were confirmed by ¹H and ¹³C NMR spectroscopy. In the ¹H NMR spectra, two characteristic doublet signals of the NH protons were observed at 9.25–8.39 ppm, while the CH signals of the thiazole and alkylamide fragments appeared at 7.24–7.19 ppm and 7.03–6.84 ppm, respectively. The ¹³C NMR spectra exhibited diagnostic signals of C=O (≈167 ppm), CCl₃ (≈102 ppm), and CH (≈71 ppm) carbons, as well as three thiazole carbon signals at ≈166, 149, and 103 ppm. The structure of compound 3a was unambiguously confirmed by single-crystal X-ray diffraction analysis, which revealed its nearly coplanar molecular geometry and a hydrogen-bonded chain motif along the [001] direction, stabilized by bifurcated N–H…O interactions.
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Synthesis, spectral characteristics, and molecular structure of N-(2,2,2-trichloro-1-((4-phenylthiazol-2-yl)amino)ethyl)carboxamides
Published:
03 December 2025
by MDPI
in The 6th International Electronic Conference on Applied Sciences
session Nanosciences, Chemistry and Materials Science
Abstract:
Keywords: 1,3-thiazole; thiourea; molecular structure; synthesis
