Sodium hydride → HCID 68577887, compound

HRID 886971Notes

Reaction equation

HRID 886971 reaction equation
[CH2:1]([N:8]([CH2:20][CH2:21][OH:22])[C:9](=[O:19])[C:10]1[C:15]([F:16])=[CH:14][CH:13]=[C:12]([Br:17])[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:19])[C:10]2[C:15]([F:16])=[CH:14][CH:13]=[C:12]([Br:17])[C:11]=2[O:22][CH2:21][CH2:20]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 68580640HCID 68580640, compound

Product 1

HCID 68577887HCID 68577887, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-benzyl-3-bromo-2,6-difluoro-N-(2-hydroxyethyl)benzamide (1.50 g, 4.05 mmol) in N,N-dimethylformamide (30 ml) under ice-cooling, 60% sodium hydride (210 mg, 5.27 mmol) was added, 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 to give the desired product (1.40 g, 98.6%) as an oil.

Workup

  1. temperaturecooling
  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-f6fba0229c6546aea8dd26763a58ee47
Source dataset
uspto-grants-2012_08
Patent number
US08247403B2

Reaction notes

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