Practical methylation procedure for (1H)-1,2,4-triazole

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.