N-Sulfinyl-p-toluenesulfonamide

[4104-47-6] C7H7NO3S2 (MW 217.29) InChI = 1S/C7H7NO3S2/c1-6-2-4-7(5-3-6)13(10,11)8-12-9/h2-5H,1H3 InChIKey = VKTSIMMJOIPMGE-UHFFFAOYSA-N (used to generate electrophilic N-tosyl aldimines;4-7 can act as an enophile in ene reactions2, 8 and as a dienophile in Diels–Alder reactions;10, 11 participates in Wittig-type reactions17) Alternate Name: 4-methyl-N-sulfinylbenzenesulfonamide. Physical Data: mp 53 °C; bp 130–140 °C/0.06 mmHg. Solubility: sol benzene, toluene, halogenated solvents. Form Supplied in: bright yellow solid; commercially available. Preparative Methods: the most common method of preparing N-sulfinyl-p-toluenesulfonamide (TsNSO) 1 is by heating p-toluenesulfonamide with excess Thionyl Chloride in benzene (eq 1).2 (1) An alternative procedure is the treatment of p-toluenesulfonamide with N-chlorosulfinylimidazole, which is derived from thionyl chloride and Imidazole (eq 2).3 The latter method benefits from shorter reaction times and better yields. (2) Handling, Storage, and Precautions: should be weighed out in a glove bag or dry box, since it readily hydrolyzes to p-toluenesulfonamide. Can be prepared just prior to use and used in situ or stored for extended periods of time in an inert environment.