N,N-Dimethylaniline → N-[4-benzyloxy-2,6-bis(trifluoromethyl)phenyl]-2-bromoacetamide

HRID 1373735Notes

Reaction equation

HRID 1373735 reaction equation
CN(C)C1C=CC=CC=1.[Br:10][CH2:11][C:12](Br)=[O:13].[CH2:15]([O:22][C:23]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[C:26]([NH2:27])=[C:25]([C:34]([F:37])([F:36])[F:35])[CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[CH2:15]([O:22][C:23]1[CH:24]=[C:25]([C:34]([F:36])([F:37])[F:35])[C:26]([NH:27][C:12](=[O:13])[CH2:11][Br:10])=[C:28]([C:30]([F:31])([F:32])[F:33])[CH:29]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 61147Bromoacetyl bromideHCID 210756004-Benzyloxy-2,6-bis(trifluoromethyl)aniline

Product 1

HCID 21075603N-[4-benzyloxy-2,6-bis(trifluoromethyl)phenyl]-2-bromoacetamideYield 64.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under an argon atmosphere, N,N-dimethylaniline (2.78 mL, 21.9 mmol) and bromoacetyl bromide (1.91 mL, 21.9 mmol) were added dropwise to a solution of 4-benzyloxy-2,6-bis(trifluoromethyl)aniline (4.90 g, 14.6 mmol) in anhydrous toluene (150 mL) under ice cooling. Immediately after the dropwise addition, the mixture was heated under reflux and then stirred for 1 hour. After cooling, the reaction mixture was filtered through Celite and the insoluble matter was washed with toluene. The residue obtained by distilling the filtrate under reduced pressure was purified by chromatography on a silica gel column (developing solvent; hexane:acetone=10:1→6:1→5:1). The crude product thus obtained was recrystallized from hexane-acetone, whereby 4.31 g (yield: 64.7%) of N-[4-benzyloxy-2,6-bis(trifluoromethyl)phenyl]-2-bromoacetamide was obtained as colorless needle-like crystals.

Workup

  1. additionImmediately after the dropwise addition
  2. temperaturethe mixture was heated
  3. temperatureunder reflux
  4. temperatureAfter cooling
  5. filtrationthe reaction mixture was filtered through Celite
  6. washthe insoluble matter was washed with toluene
  7. customThe residue obtained
  8. distillationby distilling the filtrate under reduced pressure
  9. customwas purified by chromatography on a silica gel column (developing solvent; hexane:acetone=10:1→6:1→5:1)
  10. customThe crude product thus obtained
  11. customwas recrystallized from hexane-acetone

Sources & evidence

ORD record
ord-758d94ad5a20437e9bbeb57198c2ac0d
Source dataset
uspto-grants-2007_01
Patent number
US07163944B2

Reaction notes

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