Sodium hydride → 1-Propyl-1H-imidazole-2-carbaldehyde

HRID 348691Notes

Reaction equation

HRID 348691 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[O:7].I[CH2:9][CH2:10][CH3:11].[H-].[Na+]>CN(C=O)C>[CH2:9]([N:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[O:7])[CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 249551H-imidazole-2-carbaldehydeHCID 336431-Iodopropane

Product 1

HCID 47776601-Propyl-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 1-iodopropane (1.52 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 distilled off. Then, the residue was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (600 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 distilled off
  7. customThen, the residue was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-de21a0ab307b46afac980dc9bca32271
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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