Methyl iodide → 4-cyano-N-(2-furan-2-ylphenyl)-3,N-dimethylbenzamide

HRID 558986Notes

Reaction equation

HRID 558986 reaction equation
[C:1]([C:3]1[CH:22]=[CH:21][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]2[O:17][CH:18]=[CH:19][CH:20]=2)=[O:8])=[CH:5][C:4]=1[CH3:23])#[N:2].[H-].[Na+].I[CH3:27]>CN(C=O)C>[C:1]([C:3]1[CH:22]=[CH:21][C:6]([C:7]([N:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]2[O:17][CH:18]=[CH:19][CH:20]=2)[CH3:27])=[O:8])=[CH:5][C:4]=1[CH3:23])#[N:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 574707854-Cyano-N-(2-furan-2-ylphenyl)-3-methylbenzamide

Product 1

HCID 574707864-cyano-N-(2-furan-2-ylphenyl)-3,N-dimethylbenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-cyano-N-(2-furan-2-ylphenyl)-3-methylbenzamide from Example 21B (222 mg, 0.734 mmol) in DMF (8.0 ml) was added sodium hydride (60%, 44 mg, 1.10 mmol) while cooling in an ice/water bath. The mixture was allowed to warm to room temperature and stirred for 45 min. Iodomethane (68 μl, 1.10 mmol) was added and the mixture was stirred for 18 h. The mixture was evaporated in vacuo and the residue was taken up in EtOAc, washed with brine, dried and evaporated in vacuo. The residue was purified by flash chromatography on silica (eluant pet.ether:EtOAc 80:20) to give a brown solid; yield 198 mg, 85%.

Workup

  1. temperaturewhile cooling in an ice/water bath
  2. stirringthe mixture was stirred for 18 h
  3. customThe mixture was evaporated in vacuo
  4. washwashed with brine
  5. customdried
  6. customevaporated in vacuo
  7. customThe residue was purified by flash chromatography on silica (eluant pet.ether:EtOAc 80:20)
  8. customto give a brown solid

Sources & evidence

ORD record
ord-561a477d4f9a4edda0dc30eb9b9c4675
Source dataset
uspto-grants-2011_11
Patent number
US08063038B2

Reaction notes

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