Water → 3-ETHYL-3H-IMIDAZOLE-4-CARBALDEHYDE

HRID 1186369Notes

Reaction equation

HRID 1186369 reaction equation
[NH:1]1[C:5]([CH:6]=[O:7])=[CH:4][N:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:14](I)[CH3:15].O>CN(C)C=O.C(OCC)(=O)C>[CH2:14]([N:1]1[C:5]([CH:6]=[O:7])=[CH:4][N:3]=[CH:2]1)[CH3:15].[CH2:14]([N:3]1[CH:4]=[C:5]([CH:6]=[O:7])[N:1]=[CH:2]1)[CH3:15]

Participants

8

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 764281H-Imidazole-4-carbaldehyde

Product 2

HCID 31596723-ETHYL-3H-IMIDAZOLE-4-CARBALDEHYDEYield 30%HCID 135098721-Ethyl-1H-imidazole-4-carbaldehydeYield 9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1H-Imidazole-5-carbaldehyde (300 mg, 3.12 mmol) was dissolved in N,N-dimethylformamide (4 mL). To this, potassium carbonate (862 mg, 6.24 mmol) and ethyl iodide (0.275 mL, 3.43 mmol) were added at room temperature and the mixture was stirred at the same temperature for 1.5 hours. After water was added to the reaction mixture, extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by preparative thin-layer chromatography (chloroform/methanol=20/1) to give 1-ethyl-1H-imidazole-5-carbaldehyde (115 mg, yield: 30%) and 1-ethyl-1H-imidazole-4-carbaldehyde (36 mg, yield: 9%). 1-ethyl-1H-imidazole-5-carbaldehyde

Workup

  1. washby washing with brine
  2. dry with materialdrying over anhydrous sodium sulfate
  3. customThe solvent was evaporated off under reduced pressure
  4. customthe residue was purified by preparative thin-layer chromatography (chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-4e89b32c2f034fbdb8b166bf66a9ba3b
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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