Functionalization of 2-Mercapto-5-methyl-1,3,4-thiadiazole: 2-(ω-Haloalkylthio) Thiadiazoles vs. Symmetrical Bis-Thiadiazoles

TL;DR

This paper describes the chemical modification of a thiadiazole compound to produce two new series of compounds with different structures and properties.

Contribution

The study introduces optimized methods for synthesizing two distinct classes of thiadiazole derivatives with variable chain lengths.

Findings

Two series of thiadiazole derivatives were successfully synthesized with different functional groups.

Optimized experimental conditions were developed for each compound class based on reactivity and purification requirements.

Structural properties of the products were confirmed using NMR and X-ray diffraction analysis.

Abstract

A study on the functionalisation of 2-mercapto-5-methyl-1,3,4-thiadiazole has been conducted, yielding two series of products: 2-(ω-haloalkylthio)thiadiazoles and symmetrical bis-thiadiazoles, with variable chain lengths. The experimental conditions were optimised for each class of compounds by altering the base used and the reagents’ proportions, leading to the development of separate protocols tailored to their specific reactivity and purification needs. The target halogenide reagents and bis-thiadiazole ligands were obtained either as single products or as mixtures easily separable by chromatography. Characterisation of the products was performed using 1D and 2D NMR spectra in solution, complemented by single crystal X-ray diffraction (XRD) for selected samples, to elucidate their structural properties.

Figures