Short-RInChIKey=SA-FUHFF-UHFFFADPSC-NDLIRBZKZS-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

To a suspension of 4-methylbenzenesulfonyl chloride (20.0 g, 105 mmol, 1.00 equiv) in 133 mL acetone cooled to 0 °C, a solution of sodium;azide (10.2 g, 157 mmol, 1.50 equiv) in 40 mL water was added over one hour. The mixture was slowly warmed to 21 °C overnight. The solvent was removed under reduced pressure and the aqueous phase extracted with diethyl ether (3 x 50 mL). The combined organic phases were washed with water (2 x 50 mL), saturated sodium carbonate solution (50 mL) and saturated sodium chloride solution (50 mL). After drying over magnesium sulfate, the solvent was removed under reduced pressure to give (NE)-N-diazo-4-methylbenzenesulfonamide (19.7 g, 99.9 mmol, 95% yield) as a colorless liquid.