An Updated Synthesis of the Diazo-Transfer Reagent Imidazole-1-sulfonyl Azide Hydrogen Sulfate

Potter, Garrett T.; Jayson, Gordon C.; Miller, Gavin J.; Gardiner, John M.

Abstract

Imidazole-1-sulfonyl azide and salts thereof are valuable reagents for diazo-transfer reactions, most particularly conversion of primary amines to azides. The parent reagent and its HCl salt present stability and detonation risks, but the hydrogen sulfate salt is significantly more stable. An updated procedure for the large-scale synthesis of this salt avoids isolation or concentration of the parent compound or HCl salt and will facilitate the use of hydrogen sulfate salt as the reagent of choice for diazo transfer.

Citation

Potter, G. T., Jayson, G. C., Miller, G. J., & Gardiner, J. M. (2016). An Updated Synthesis of the Diazo-Transfer Reagent Imidazole-1-sulfonyl Azide Hydrogen Sulfate. Journal of Organic Chemistry, 81(8), 3443-3446. https://doi.org/10.1021/acs.joc.6b00177

• Journal Article Type: Article
• Online Publication Date: Mar 29, 2016
• Publication Date: Apr 15, 2016
• Deposit Date: Jun 14, 2023
• Journal: The Journal of Organic Chemistry
• Print ISSN: 0022-3263
• Electronic ISSN: 1520-6904
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 81
• Issue: 8
• Pages: 3443-3446
• DOI: https://doi.org/10.1021/acs.joc.6b00177
• Keywords: Organic Chemistry