Sodium hydride → HCID 22324258, compound

HRID 1453650Notes

Reaction equation

HRID 1453650 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7]Br.[NH:12]1[C:18](=[O:19])[CH2:17][CH2:16][CH2:15][C:14]2[CH:20]=[CH:21][CH:22]=[CH:23][C:13]1=2>CN(C)C=O>[Br:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7][N:12]1[C:18](=[O:19])[CH2:17][CH2:16][CH2:15][C:14]2[CH:20]=[CH:21][CH:22]=[CH:23][C:13]1=2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 699793-Bromobenzyl bromideHCID 2485801,3,4,5-Tetrahydro-2H-1-benzazepin-2-one

Product 1

HCID 22324258HCID 22324258, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 0.1 g (4 mmole) sodium hydride and 0.75 g (3.0 mmole) 3-bromobenzyl bromide in 5 mL dimethylformamide was added 0.438 g (2.72 mmole) solid 1,3,4,5-tetrahydro-benzo[b]azepin-2-one. The mixture was cooled in a water bath, then it was stirred at 23° for 1 hr. The solvent was removed under reduced pressure and the residue was partitioned between 30 mL ethyl acetate and 5 mL water. The organic phase was washed with 5 mL water, 5 mL saturated sodium chloride, dried (mgSO4) and concentrated under reduced pressure. The residue was recrystallized from hexane to provide the title compound, 0.658 g, m.p. 81-82°.

Workup

  1. temperatureThe mixture was cooled in a water bath
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was partitioned between 30 mL ethyl acetate and 5 mL water
  4. washThe organic phase was washed with 5 mL water, 5 mL saturated sodium chloride
  5. customdried (mgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-02c8fccac3b6481e97f94f9a851a0af1
Source dataset
uspto-grants-2009_01
Patent number
US07476675B2

Reaction notes

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