4-Toluenesulfonyl chloride → p-Toluenesulfonyl azide

Participants

Reaction Steps

To a solution of tosyl chloride (4 g, 21 mmols) in acetone (60 ml) was added at 0-5 C a solution of sodium azide (1.37 g, 21 mmols) and the resulting solution was stirred at that temperature for 2 hours. Acetone was removed and the aqueous mixture was extracted with ether three times. The combined extracts were dried over MgSO4. Evaporation of solvents provided tosyl azide (4 g, 97%). (Eur. J. Org. Chem. 2003, 821-832.)

Provenance & Evidence