Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 5
1,053
Views
12
CrossRef citations to date
0
Altmetric
Original Articles

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

, &
Pages 738-745 | Received 14 Sep 2007, Published online: 15 Feb 2008
 

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.

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.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.