Iodoethane → 1-ethyl-1H-imidazole-2-carbaldehyde

HRID 348689Notes

Reaction equation

HRID 348689 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[O:7].I[CH2:9][CH3:10].[H-].[Na+]>CN(C=O)C>[CH2:9]([N:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[O:7])[CH3:10]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 249551H-imidazole-2-carbaldehyde

Product 1

HCID 110623771-ethyl-1H-imidazole-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (15 ml), 2-imidazole carboxaldehyde (500 mg) was dissolved. Then, the solution was added with iodoethane (1.25 ml) and sodium hydride (208 mg), followed by stirring at room temperature for 5 days. After completion of the reaction, the solvent was distilled off and the residue was then added with chloroform, followed by washing with water and saturated saline solution. The resultant was dried with anhydrous sodium sulfate, and the solvent was then distilled off. The residue was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (280 mg) as a yellow oily substance.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off
  3. additionthe residue was then added with chloroform
  4. washby washing with water and saturated saline solution
  5. dry with materialThe resultant was dried with anhydrous sodium sulfate
  6. distillationthe solvent was then distilled off
  7. customThe residue was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-8f05e86cc5a04e3182262c76e194d2e2
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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