4-((5-(1-(4-Fluorophenyl)-5-methyl-1H-1,2,3-triazol-4-yl)-1,3,4-thiadiazol-2-yl)amino)benzenesulfonic acid: unexpected synthesis, structure elucidation and antimicrobial activity

Abstract

Unexpected ring closure of 2-(1-(4-fluorophenyl)-5-methyl-1H-1,2,3-triazole-4-carbonyl)-N-phenylhydrazine-1-carbothioamide (3) on exposure to sulfuric acid at room temperature for an extended duration (12 h) gave 4-((5-(1-(4-fluorophenyl)-5-methyl-1H-1,2,3-triazol-4-yl)-1,3,4-thiadiazol-2-yl)amino)benzenesulfonic acid (4) in 75% yield. The use of sulfuric acid led to sulfonation at the para-position of the benzene ring in phenyl isothiocyanate. The crystal structure comprises two independent types of molecules of 4 and two disordered ether solvent molecules. The synthesized benzenesulfonic acid inhibits the growth of both Listeria monocytogenes and Escherichia coli and its activity was comparable to those obtained for ampicillin and vancomycin.

Graphical Abstract

Keywords:

• 4-(1,3,4-Thiadiazol-2-yl)amino)benzenesulfonic acid
• phenyl isothiocyanate
• 1,2,3-triazole
• antimicrobial activity
• X-ray crystallography

Acknowledgement

B.F. Abdel-Wahab and H.A. Mohamed thank the National Research Center, Dokki, Giza, Egypt for support.

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

G. A. El-Hiti extends his appreciation to the Deanship of Scientific Research, King Saud University for funding through the Vice Deanship of Scientific Research Chairs, Research Chair of Cornea.