Dimethylformamide → HCID 19001732, compound

Participants

Reaction Steps

A mixture of 100 grams (655 mmol.) of vinylbenzyl chloride (mixture of m- and p-isomers), 42.6 grams (655 mmol.) of sodium azide and 500 mi. of dimethylformamide was stirred at room temperature for 24 hours. Ethyl ether, 500 mi., was then added and the mixture was extracted with two 300-mi. portions of water. The combined aqueous phases were extracted with 500 mi. of ethyl ether, and the combined organic layers were dried over magnesium sulfate, filtered and evaporated to yield 105 grams (100% of theoretical) of vinylbenzyl azide. The structure was confirmed by proton and carbon-13 nuclear magnetic resonance spectroscopy and infrared spectroscopy.

Provenance & Evidence