Practical Methylation Procedure for (1H)‐1,2,4‐Triazole

Abstract

Conversion of (1H)‐1,2,4‐triazole to its sodium salt with methanolic sodium methoxide is followed by reaction with iodomethane. A scalable approach that overcomes problems associated with water‐soluble starting material and water‐soluble product combined continuous extraction (chloroform/water) with a final short‐path distillation under a controlled vacuum to obtain spectroscopically pure 1‐methyl‐1,2,4‐triazole in 63% yield. Adaptation to microwave synthesis conditions, while providing a faster reaction time, offers no product yield or purification advantages over the conventional approach described. Conversions of this product to related derivatives such as 1,4‐dimethyl‐1,2,4‐triazolium iodide and 1‐methyl‐1,2,4‐triazolium hydrochloride are readily achieved.

Keywords:

• 1‐methyl‐1,2,4‐triazole
• regioselective alkylation
• sequential continuous extraction
• short‐path distillation
• 1,2,4‐triazole sodium salt

Acknowledgments

The authors acknowledge the Office of Naval Research (ONR, Project Number N0001406MP20093) and the Air Force Research Laboratory (AFRL/RZSP, Edwards AFB, CA) for their generous financial support.