4-Toluenesulfonyl chloride → p-Toluenesulfonyl azide

Participants

Reaction Steps

Sodium azide (22.5 g, 0.35 mol) was dissolved in H2O(65 ml) and diluted with 90% aqueous ethanol (130 ml). To this mixture, a solution of p-toluenesulfonyl chloride (60 g, 0.32 mol) in ethanol (300 ml) was added dropwise at 10°-25° C. and stirring was continued for 2.5 hours at room temperature. The reaction mixture was evaporated under reduced pressure, the resultant residue was washed with H2O for several times, dried over anhydrous MgSO4 and filtered with suction to give the title compound as a colorless oil; yield: 50.7 g.

Provenance & Evidence