Methyl iodide → 2-Benzyl-N-(3,5-bis-trifluoromethyl-benzyl)-N-methyl-benzamide

HRID 1358613Notes

Reaction equation

HRID 1358613 reaction equation
[CH2:1]([C:8]1[CH:31]=[CH:30][CH:29]=[CH:28][C:9]=1[C:10]([NH:12][CH2:13][C:14]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[C:16]([C:24]([F:27])([F:26])[F:25])[CH:15]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:32][Si](C)(C)[N-][Si](C)(C)C.[K+].CI.C(OCC)(=O)C>CN(C)C=O>[CH2:1]([C:8]1[CH:31]=[CH:30][CH:29]=[CH:28][C:9]=1[C:10]([N:12]([CH2:13][C:14]1[CH:15]=[C:16]([C:24]([F:25])([F:26])[F:27])[CH:17]=[C:18]([C:20]([F:22])([F:23])[F:21])[CH:19]=1)[CH3:32])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 3251421Potassium bis(trimethylsilyl)amideHCID 98243732-Benzyl-N-(3,5-bis-trifluoromethyl-benzyl)-benzamide

Product 1

HCID 98684212-Benzyl-N-(3,5-bis-trifluoromethyl-benzyl)-N-methyl-benzamideYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 100 mg (0.23 mmol) 2-benzyl-N-(3,5-bis-trifluoromethyl-benzyl)-benzamide in 1 ml N,N-dimethylformamide at 0° C. were added 50 mg (0.25 mmol) potassium hexamethyldisilazide. Stirring was continued for 1 h at this temperature and 0.016 ml (0.25 mmol) methyl iodide were added. After stirring for 3 h at room temperature, ethyl acetate was added. The mixture was washed with brine, dried (magnesium sulfate) and evaporated. The solvent was removed in vacuo and the residue was purified by flash chromatography to give 90 mg (87%) of the title compound as a colourless oil.

Workup

  1. additionwere added
  2. stirringAfter stirring for 3 h at room temperature
  3. washThe mixture was washed with brine
  4. dry with materialdried (magnesium sulfate)
  5. customevaporated
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-403329ad8e0949c3b6550edd634050ef
Source dataset
uspto-grants-2003_07
Patent number
US06596773B2

Reaction notes

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