Methyl iodide → 1-methyl-4-phenyl-1H-imidazole

HRID 2194832Notes

Reaction equation

HRID 2194832 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:12](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C.CCOC(C)=O>[CH3:12][N:10]1[CH:11]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=[CH:9]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 178418822HCID 178418822, compound

Product 1

HCID 27487821-methyl-4-phenyl-1H-imidazole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-phenyl-1H-imidazole 41 (2.01 g, 13.9 mmol) in DMF (30 mL) containing cesium carbonate (6.05 g, 18.6 mmol) at room temperature was added iodomethane (0.950 mL, 15.3 mmol). The reaction mixture was stirred at room temperature for 5 h, diluted with EtOAc, washed with water (1×), brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (70% to 100% EtOAc in hexanes) gave 1-methyl-4-phenyl-1H-imidazole 42. Mass spectrum: calculated for C10H10N 158.1; found 159.2 (M++1).

Workup

  1. washwashed with water (1×), brine (1×)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash column chromatography on silica gel (70% to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-476b3244c1eb4b05b015ce3f9f887c08
Source dataset
uspto-grants-2012_12
Patent number
US08334317B2

Reaction notes

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