N-(tert-Butoxycarbonyl)sulfamoyl Chloride

[147000-89-3] C5H10ClNO4S (MW 215.65) InChI = 1S/C5H10ClNO4S/c1-5(2,3)11-4(8)7-12(6,9)10/h1-3H3,(H,7,8) InChIKey = KAJZZLBZXOBEMD-UHFFFAOYSA-N (sulfamoylating reagent used for the conversion of alcohols to sulfamates, amines to sulfamides, hydroxylamine to hydroxysulfamides) Alternate Names: N-Boc-sulfamoyl chloride, tert-butyl N-chlorosulfonylcarbamate, tert-butoxycarbamoylsulfamoyl chloride, N-chlorosulfonylcarbamic acid tert-butyl ester. Physical Data: mp 67–70 °C. Solubility: sol CH2Cl2, CHCl3, THF, benzene, toluene. Analysis of Reagent Purity: 1H and 13C NMR. Preparation and Purification: N-(tert-butoxycarbonyl)sulfamoyl chloride (1) is prepared by addition of tert-butanol to chlorosulfonyl isocyanate (CSI) (eq 1). In a typical preparative method, tert-butanol (1 equiv) is added dropwise to a solution of CSI (1 equiv) in CH2Cl2 (1.2–2.3 M CSI) at 0 °C and the mixture is stirred for 30 min to 1 h. Other nonprotic solvents can be used and the reaction is typically quantitative. The resulting solution of N-Boc-sulfamoyl chloride is usually treated in situ with the desired nucleophile. It can be purified by crystallization from CH2Cl2/hexanes.1, 2 (1) Handling, Storage, and Precautions: the title compound 1 is extremely moisture sensitive, should be stored in an inert atmosphere, and is preferably freshly prepared before use.