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

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• 作者：Garrett T. Potter ; Gordon C. Jayson ; Gavin J. Miller ; John M. Gardiner
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：April 15, 2016
• 年：2016
• 卷：81
• 期：8
• 页码：3443-3446
• 全文大小：265K
• 年卷期：0
• ISSN：1520-6904

文摘

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.