Sodium hydride → HCID 68580572, compound

HRID 886976Notes

Reaction equation

HRID 886976 reaction equation
[CH2:1]([N:8]([CH2:20][CH2:21][OH:22])[C:9](=[O:19])[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[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[CH:15]=[CH:14][C:13]([F:16])=[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 68578370HCID 68578370, compound

Product 1

HCID 68580572HCID 68580572, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-benzyl-3-bromo-2,4-difluoro-N-(2-hydroxyethyl)benzamide (4.57 g, 12.3 mmol) in N,N-dimethylformamide (60 ml) was added under ice-cooling sodium hydride (60%, 593 mg, 14.8 mmol), and the mixture was stirred for 2 hr. The reaction mixture was poured into ice water, and the mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous sodium sulfate, and 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 (3.23 g, 75.0%) as an oil.

Workup

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

Sources & evidence

ORD record
ord-383382fc6caf4a6ba285e13632b69d0a
Source dataset
uspto-grants-2012_08
Patent number
US08247403B2

Reaction notes

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