Methyl iodide → Ethyl 1-methyl-2-phenyl-1H-imidazole-4-carboxylate

HRID 1816623Notes

Reaction equation

HRID 1816623 reaction equation
[C:1]1([C:7]2[NH:8][C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:19]I.[Cl-].[NH4+]>CN(C)C=O.O>[CH3:19][N:11]1[CH:10]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:8]=[C:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 1512596Ethyl 2-phenyl-1H-imidazole-5-carboxylate

Product 1

HCID 22493986Ethyl 1-methyl-2-phenyl-1H-imidazole-4-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3.5 g of ethyl 2-phenyl-1H-5-imidazolecarboxylate was dissolved in 30 ml N,N-dimethylformamide. 0.71 g of sodium hydride was added thereto under ice-cooling, followed by stirring at room temperature for 1 hour. The reaction solution was ice-cooled again and 1.5 ml methyl iodide was added, followed by stirring at room temperature for 30 minutes. Water and aqueous ammonium chloride solution were added to the reaction solution, followed by extracting with ethyl acetate. The ethyl acetate layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography, to give 0.6 g of ethyl 1-methyl-2-phenyl-1H-4-imidazole carboxylate with hexane:ethyl acetate=8:1 and 2.2 g of ethyl 1-methyl-2-phenyl-1H-5-imidazolecarboxylate with hexane:ethyl acetate=1:1.

Workup

  1. temperatureunder ice-cooling
  2. temperaturecooled again
  3. stirringby stirring at room temperature for 30 minutes
  4. extractionby extracting with ethyl acetate
  5. washThe ethyl acetate layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8c4240d37dd94d08aad5597d10bb978f
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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