Methyl iodide → N-(2-Benzoyl-4-chloro-phenyl)-2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-isobutyramide

HRID 1358601Notes

Reaction equation

HRID 1358601 reaction equation
[C:1]([C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[NH:16][C:17](=[O:35])[C:18]([C:21]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:22]=1)([CH3:20])[CH3:19])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:38]I>CN(C)C=O>[C:1]([C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[N:16]([CH3:38])[C:17](=[O:35])[C:18]([C:21]1[CH:22]=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:24]=[C:25]([C:27]([F:30])([F:28])[F:29])[CH:26]=1)([CH3:20])[CH3:19])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18185376N-(2-benzoyl-4-chloro-phenyl)-2-(3,5-bis-trifluoromethyl-phenyl)-isobutyramide

Product 1

HCID 9914870N-(2-Benzoyl-4-chloro-phenyl)-2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-isobutyramideYield 32.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 154 mg (0.3 mmol) of N-(2-benzoyl-4-chloro-phenyl)-2-(3,5-bis-trifluoromethyl-phenyl)-isobutyramide in 1 ml dimethylformamide were added 26 mg (0.6 mmol) sodium hydride (55% suspension in mineral oil). After 30 min stirring at room temperature 85 mg of methyl iodide (0.6 mmol) were added and the reaction mixture was stirred at 80° C. overnight. The solvent was evaporated under reduced pressure and the residue was purified by flash chromatography to yield 51 mg (32%) of the title compound as white crystals. M.p. 89-91° C.

Workup

  1. additionwere added
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-ef4baf8d86ed49b9ba9d43adeb77c9c5
Source dataset
uspto-grants-2003_07
Patent number
US06596773B2

Reaction notes

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