IONUT VALENTIN LEDETI, VASILE NICOLAE BERCEAN, VALENTIN BADEA, MIHAELA BALAN, CAROL CSUNDERLIK<br>The Alkylation of 1H-5-mercapto-3-phenyl -1,2,4-triazole and <br>4H-4-amino-5-mercapto-3-phenyl -1,2,4-triazole

IONUT VALENTIN LEDETI, VASILE NICOLAE BERCEAN, VALENTIN BADEA, MIHAELA BALAN, CAROL CSUNDERLIK
The Alkylation of 1H-5-mercapto-3-phenyl -1,2,4-triazole and
4H-4-amino-5-mercapto-3-phenyl -1,2,4-triazole

Abstract:

The alkylation of in situ prepared sodium salts of 1H-5-mercapto-3-phenyl-1,2,4-triazole (1a) and 4H-4-amino-5-mercapto-3-phenyl-1,2,4-triazole (2a) with ethyl chloroacetate in absolute ethanol leads with good yields to 1H-5-ethoxycarbonyl-methylsulfanyl-3-phenyl-1,2,4-triazole (3a) and 4H-4-amino-3-ethoxycarbonyl-methylsulfanyl-5-phenyl-1,2,4-triazole (4a). The alkaline hydrolysis of the esters (3a, 4a) leads to 1H-5-carboxy-methylsulfanyl-3-phenyl-1,2,4-triazole (6a) and 4H-4-amino-5-carboxy-methylsulfanyl-3-phenyl-1,2,4-triazole (5a), respectively. All the compounds were characterized by mass, IR, 1H-NMR and 13C-NMR spectroscopy, and the confirmation of S-alkylation was proven through 2D NMR spectra. Keywords: S-alkylation, mercapto-triazoles, amino-mercapto-triazoles, acetic acid derivatives, NMR data

Issue: 2010, Volume 61, Issue 9

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IONUT VALENTIN LEDETI, VASILE NICOLAE BERCEAN, VALENTIN BADEA, MIHAELA BALAN, CAROL CSUNDERLIKThe Alkylation of 1H-5-mercapto-3-phenyl -1,2,4-triazole and 4H-4-amino-5-mercapto-3-phenyl -1,2,4-triazole

IONUT VALENTIN LEDETI, VASILE NICOLAE BERCEAN, VALENTIN BADEA, MIHAELA BALAN, CAROL CSUNDERLIK
The Alkylation of 1H-5-mercapto-3-phenyl -1,2,4-triazole and
4H-4-amino-5-mercapto-3-phenyl -1,2,4-triazole