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

HRID 2035698Notes

Reaction equation

HRID 2035698 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

5

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 541183906-Fluoro-3-iodo-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one

Product 1

HCID 190256673-Azido-6-fluoro-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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.

Workup

  1. customa precipitate formed
  2. filtrationwhich was filtered off
  3. washwashed with water
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-02df447e8eb34b6b8b9cb962fe70024a
Source dataset
uspto-grants-2013_11
Patent number
US08575150B2

Reaction notes

Loading…