Methyl iodide → 4-Cyano-3,N-dimethyl-N-(4-trifluoromethyl-phenyl)-benzamide

HRID 220979Notes

Reaction equation

HRID 220979 reaction equation
[C:1]([C:3]1[CH:21]=[CH:20][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[O:8])=[CH:5][C:4]=1[CH3:22])#[N:2].[H-].[Na+].[CH3:25]I>CN(C=O)C>[C:1]([C:3]1[CH:21]=[CH:20][C:6]([C:7]([N:9]([CH3:25])[C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:18])([F:17])[F:19])=[CH:12][CH:11]=2)=[O:8])=[CH:5][C:4]=1[CH3:22])#[N:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57555385HCID 57555385, compound

Product 1

HCID 575552024-Cyano-3,N-dimethyl-N-(4-trifluoromethyl-phenyl)-benzamideYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

4-Cyano-3-methyl-N-(4-trifluoromethyl-phenyl)-benzamide from Example E118.1 (1.10 g, 3.6 mmol) was dissolved in DMF (10 ml) and cooled down to 0° C. Sodium hydride (60% dispersion in oil, 174 mg, 4.3 mmol) was added and the mixture was stirred for 30 min at room temperature. Methyl iodide (0.27 ml, 4.3 mmol) was added and the mixture was stirred for 20 h. Solvents were removed in vacuo and azeotroped with toluene. The residue was re-dissolved in EtOAc, washed with brine, dried and concentrated in vacuo to yield the title compound (1.08 g, 94%).

Workup

  1. stirringthe mixture was stirred for 20 h
  2. customSolvents were removed in vacuo
  3. customazeotroped with toluene
  4. dissolutionThe residue was re-dissolved in EtOAc
  5. washwashed with brine
  6. customdried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-18c98bcaad27445c96d68d04bb4e4809
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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