The reaction of 5-substituted amino-1,3,4-thiodiazoline-2-thiones with benzoyl chloride was studied. The effects of factors such as solvent type, base type, temperature, and time on the reaction conditions have been analysed. According to the experimental results, reactions in the presence of dichloromethane solvent and pyridine base at 40 °C for 4 hours had the highest product yield (85–88%). The composition of the synthesised S- and N3-benzoyl derivatives was studied using FTIR-spectral analysis. The obtained compounds are promising for use as intermediates in the synthesis of further biologically active substances.