4-Toluenesulfonyl chloride → p-Toluenesulfonyl azide

Participants

Reaction Steps

After dissolving 22.5 g (0.35 mole) of sodium azide in a small amount of water, the resulting solution was diluted with 130 ml of 90% hydrous ethanol. An ethanol solution having 60 g (0.32 mole) of p-toluenesulfonyl chloride dissolved therein was added dropwise to the solution at 10 to 25° C. They were reacted at room temperature for 2.5 hours. An oil obtained by concentrating the reaction mixture under reduced pressure was washed with water several times and then, dried over anhydrous magnesium sulfate. The desiccant was then removed, whereby 50.7 g of p-toluenesulfonyl azide was obtained as a colorless oil.

Provenance & Evidence