Methyl iodide → N-methyl-N-(2-methyl-4-nitrophenyl)-benzamide

HRID 1071733Notes

Reaction equation

HRID 1071733 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[NH:11][C:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:20](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C=O)C>[CH3:20][N:11]([C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[CH3:1])[C:12](=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 2835288N-(2-methyl-4-nitrophenyl)benzamide

Product 1

HCID 22064386N-methyl-N-(2-methyl-4-nitrophenyl)-benzamideYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(2-methyl-4-nitrophenyl)benzamide (Example 1099A) (0.38 g, 1.48 mmol) in DMF (2 mL) was added cesium carbonate (1.2 g, 3.68 mmol) followed by methyl iodide (0.12 mL, 1.9 mmol). The reaction mixture was stirred at room temp for 2 hr, extracted with EtOAc, washed with water and brine, dried and concentrated in vacuo to give N-methyl-N-(2-methyl-4-nitrophenyl)-benzamide (0.38 g, 95%). ES-MS (M+H)+=271.

Workup

  1. extractionextracted with EtOAc
  2. washwashed with water and brine
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eaf4ef1de35f440e94d22b636940f81a
Source dataset
uspto-grants-2005_06
Patent number
US06906063B2

Reaction notes

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