Methyl iodide → 1-Methyl-5-phenyl-1H-imidazole

HRID 2104954Notes

Reaction equation

HRID 2104954 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.[H-].[Na+].I[CH3:15]>C1COCC1.CCOC(C)=O>[CH3:15][N:8]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:11][N:10]=[CH:9]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178418822HCID 178418822, compound

Product 1

HCID 37463431-Methyl-5-phenyl-1H-imidazoleYield 30.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-phenylimidazole (500 mg, 3.47 mmol) in 10 mL THF at rt, was added 60% NaH (146 mg, 3.64 mmol). The mixture was stirred at rt for 5 min, then iodomethane (238 μL, 3.82 mmol) was added. The mixture was stirred at rt for 30 min, then was diluted with EtOAc. The organic phase was washed with H2O and brine, dried (Na2SO4) and concentrated. The crude residue was purified by flash chromatography (column #1: 0 to 10% MeOH/CH2Cl2 gradient, column #2: 1 to 2 to 5% MeOH/EtOAc, stepwise gradient) to afford 352 mg of Intermediate 13.1 and 166 mg of Intermediate 13.2.

Workup

  1. stirringThe mixture was stirred at rt for 30 min
  2. washThe organic phase was washed with H2O and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude residue was purified by flash chromatography (column #1

Sources & evidence

ORD record
ord-5cf778ba069a472fa6710d8474aae64a
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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