Sodium hydride → HCID 68578792, compound

HRID 886839Notes

Reaction equation

HRID 886839 reaction equation
[CH2:1]([N:8]([CH2:19][CH2:20][OH:21])[C:9](=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Br:16])[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]=[CH:14][CH:13]=[C:12]([Br:16])[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 68578657HCID 68578657, compound

Product 1

HCID 68578792HCID 68578792, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-benzyl-3-bromo-2-fluoro-N-(2-hydroxyethyl)benzamide (11.4 g, 32.4 mmol) in N,N-dimethylformamide (160 ml) was added under ice-cooling sodium hydride (60%, 1.68 g, 42.1 mmol), and the mixture was stirred under ice-cooling for 1 hr. 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=1:1) to give the desired product (8.08 g, 74.8%) 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
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-3e9e7abd05234bcda5c1688657425ecb
Source dataset
uspto-grants-2012_08
Patent number
US08247403B2

Reaction notes

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