Sodium hydride → HCID 68578555, compound

HRID 886884Notes

Reaction equation

HRID 886884 reaction equation
[CH2:1]([N:8]([CH2:19][CH2:20][OH:21])[C:9](=[O:18])[C:10]1[CH:15]=[C:14]([Br:16])[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[CH:15]=[C:14]([Br:16])[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 60740620HCID 60740620, compound

Product 1

HCID 68578555HCID 68578555, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-benzyl-5-bromo-2-fluoro-N-(2-hydroxyethyl)benzamide (4.70 g, 13.3 mmol) in N,N-dimethylformamide (100 ml) was added under ice-cooling sodium hydride (60%, 691 mg, 17.3 mmol), and the mixture was stirred under ice-cooling for 1 hr, and poured into ice water. The mixture was extracted with ethyl acetate and the extract was washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the desired product (4.20 g, 96.3%) as an oil.

Workup

  1. temperaturecooling for 1 hr
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-06f60878b1994deda3a7b4c557e95ccc
Source dataset
uspto-grants-2012_08
Patent number
US08247403B2

Reaction notes

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