Synthesis, Structural Characterization, and Thermal Stability Investigation of Methoxybenzamide Derivatives Containing the 5-Mercapto-1,3,4-Thiadiazol-2-yl Group

Abstract

Compounds with a methoxy benzamide structure contain a methoxy group (–OCH₃) and an amide functional group (–CONH₂) within a benzene ring. This causes the compound to exhibit a complex structure with polar and nonpolar characteristics. These compounds are significant in pharmaceutical chemistry, biological research, and chemical synthesis. Due to its active properties, the “N–C–S” linkage in the thiazole ring can chelate metal ions. The antimicrobial activity of benzamide compounds derived from thiazoles and their wide applications in medicine increases the importance of methoxybenzamide derivetives. In this study, 5-amino-1,3,4-thiadiazole-2-thiol compounds were reacted with 2-methoxy, 3-methoxy, and 4-methoxybenzoyl chloride in toluene under a reflux condenser, resulting in the synthesis of methoxybenzamide derivatives (a, b, c). The structural characterization of the obtained methoxybenzamide (a, b, c) compounds were performed using FTIR, LC/MS-ESI, 1H NMR, 13C APT spectroscopy, and elemental analysis. Additionally, the thermal stability of the synthesized methoxybenzamide compounds was investigated through thermal analysis (TGA/DTA/DrTG).