title: An Updated Synthesis of the Diazo-Transfer Reagent Imidazole-1-sulfonyl Azide Hydrogen Sulfate.
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.
authors.affiliation: Manchester Institute of Biotechnology and School of Chemistry, The University of Manchester , 131 Princess Street, Manchester M1 7DN, U.K.
authors.forename: Garrett T
authors.initials: GT
authors.lastname: Potter
authors.affiliation: Institute of Cancer Sciences, Faculty of Medical and Human Sciences, The University of Manchester , Manchester M20 4BX, U.K.
authors.forename: Gordon C
authors.initials: GC
authors.lastname: Jayson
authors.affiliation: Manchester Institute of Biotechnology and School of Chemistry, The University of Manchester , 131 Princess Street, Manchester M1 7DN, U.K.
authors.forename: Gavin J
authors.initials: GJ
authors.lastname: Miller
authors.affiliation: Manchester Institute of Biotechnology and School of Chemistry, The University of Manchester , 131 Princess Street, Manchester M1 7DN, U.K.
authors.forename: John M
authors.initials: JM
authors.lastname: Gardiner
mesh_terms: D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001386:Azides / Q000138:chemical synthesis* / Q000737:chemistry; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013450:Sulfones / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001372:Aza Compounds; D001386:Azides; D007093:Imidazoles; D007202:Indicators and Reagents; D013450:Sulfones; C580844:imidazole-1-sulfonyl azide