Sodium Azide → 3-Azido-4-phenylcarbostyril

Reaction equation

[C:1]([C:9]1[CH:19]=[CH:18][CH:17]=[CH:16][C:10]=1[NH:11][C:12](=[O:15])[CH2:13]Br)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:20]=[N+:21]=[N-:22].[Na+].[OH-].C([N+](C)(C)C)C1C=CC=CC=1>CO>[N:20]([C:13]1[C:12](=[O:15])[NH:11][C:10]2[C:9]([C:1]=1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N+:21]=[N-:22]

Participants

Procedure

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.