Dimethylformamide → 3-Azido-6-fluoro-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one

Reaction equation

CN(C=O)C.[F:6][C:7]1[C:12]2[CH2:13][CH2:14][CH:15](I)[C:16](=[O:18])[NH:17][C:11]=2[CH:10]=[CH:9][CH:8]=1.[N-:20]=[N+:21]=[N-:22].[Na+]>O>[N:20]([CH:15]1[CH2:14][CH2:13][C:12]2[C:7]([F:6])=[CH:8][CH:9]=[CH:10][C:11]=2[NH:17][C:16]1=[O:18])=[N+:21]=[N-:22]

Participants

Procedure

DMF (300 ml) was added to a mixture of 6-fluoro-3-iodo-1,3,4,5-tetrahydro-1-benzazepin-2-one (42.5 g) and sodium azide (13.59 g, 209 mmol) at room temperature and the reaction was stirred overnight. The mixture was diluted with water (2000 mL) and a precipitate formed, which was filtered off and washed with water. The precipitate was taken up in dichloromethane and washed with brine, dried over Na2SO4, filtered, and concentrated. The crude 3-Azido-6-fluoro-1,3,4,5-tetrahydro-1-benzazepin-2-one was isolated as a dark brown solid. Residual DMF remains in the sample, which was used without further manipulation in the next reaction.