Sodium Azide → HCID 14227209, compound

Participants

Reaction Steps

To a stirred solution of sodium azide (1.32 g) in water (5 ml) at 0° C. was added a solution of 10-undecenoyl chloride (4.30 ml) in dioxane (10 ml). The mixture was stirred for 45 minutes, and poured into ice water (100 ml). The mixture was extracted twice with benzene (50 ml), and the combined extracts were washed with ice water (25 ml), dried (MgSO4), and filtered. The filtrate was heated to reflux under a Dean-Stark trap, removing the first 30 ml of distillate. After 30 minutes at reflux, the reaction was cooled and evaporated, to provide 9-decenyl icocyanate as a colorless oil. This isocyanate was dissolved in DMF (5 ml) and added to a slurry of N-methylhydroxylamine hydrochloride (1.70 g) and triethylamine (2.84 ml) in DMF (20 ml). After two hours, the reaction mixture was filtered through Celite and quenched with water. The resulting solids were collected by filtration, washed with water, and recrystallized from ethyl acetate to provide the title compound as a white solid (1.35 g), mp 58°-59° C.

Provenance & Evidence