Sodium hydride → 4-benzyl-6-bromo-3,4-dihydro-1,4-benzoxazepine-5 (2H)-one

HRID 886889Notes

Reaction equation

HRID 886889 reaction equation
[CH2:1]([N:8]([CH2:19][CH2:20][OH:21])[C:9](=[O:18])[C:10]1[C:15]([Br:16])=[CH:14][CH:13]=[CH:12][C:11]=1F)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+]>CN(C)C=O>[CH2:1]([N:8]1[C:9](=[O:18])[C:10]2[C:15]([Br:16])=[CH:14][CH:13]=[CH:12][C:11]=2[O:21][CH2:20][CH2:19]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 68578409N-benzyl-6-bromo-2-fluoro-N-(2-hydroxyethyl)benzamide

Product 1

HCID 685778484-benzyl-6-bromo-3,4-dihydro-1,4-benzoxazepine-5 (2H)-oneYield 33.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-benzyl-6-bromo-2-fluoro-N-(2-hydroxyethyl)benzamide (15.5 g, 44.0 mmol) in N,N-dimethylformamide (200 ml) was added sodium hydride (60%, 2.29 g, 57.2 mmol) under ice-cooling, and the mixture was stirred for 1 hr under ice-cooling. The reaction mixture was poured into ice water, and the mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give the desired product (4.94 g, 33.8%) as an oil.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-cbb202ad0395452bb16abf7563e7c748
Source dataset
uspto-grants-2012_08
Patent number
US08247403B2

Reaction notes

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