Sodium Azide → 3-Azido-4-phenylcarbostyril

Participants

Reaction Steps

To a hot solution of 98.5 g. of 2'-benzoyl-2-bromo-acetanilide in 2 l methanol was added in one portion 39.0 g. of sodium azide. The mixture was heated to a slow reflux on a steam bath for 20 minutes. As the mixture cooled partially to room temperature, 18 ml. of benzyltrimethylammonium hydroxide (35% methanolic solution) was added. After standing overnight at room temperature, the orange-yellow needles that formed were collected, washed with methanol and dried at 60° C.; yield 76.6 g. (94%) of 3-azido-4-phenylcarbostyril, having a melting point of 120° - 140° dec. to high melting solid.

Provenance & Evidence