Ethanol → p-Toluenesulfonyl azide

Participants

Reaction Conditions

Reaction Steps

71.5 g of sodium azide was dissolved in 200 mL of water and mixed with 400 mL of 90% ethanol in a 2 L Erlenmeyer flask. To this solution, 1 L of a 99% ethanol solution containing 190.5 g of tosyl chloride heated to 45° C., was added with stirring, and stirring was continued at room temperature for 2.5 hours. From the reaction mixture, ethanol was evaporated under reduced pressure, and to the residue, 1.2 L of water was added, whereupon an oily azide was separated by means of a separatory funnel, washed with water, dried by anhydrous sodium sulfate and subjected to aspiration filtration to obtain 160 g of colorless p-toluenesulfonyl azide.

Provenance & Evidence