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 ml. of dimethylformamide was stirred at room temperature for 24 hours. Ethyl ether, 500 ml., was then added and the mixture was extracted with two 300ml. portions of water. The combined aqueous phases were extracted with 500 ml. 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