Water → 1-Benzyl-2-methylimidazole-4-carboxaldehyde

HRID 453564Notes

Reaction equation

HRID 453564 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([CH:7]=[O:8])[N:6]=1.[H-].[Na+].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>CN(C)C=O>[CH2:11]([N:3]1[CH:4]=[C:5]([CH:7]=[O:8])[N:6]=[C:2]1[CH3:1])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 178418999HCID 178418999, compound

Product 1

HCID 136062421-Benzyl-2-methylimidazole-4-carboxaldehydeYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-methyl-1H-imidazole-4-carbaldehyde (5.50 g) in N,N-dimethylformamide (100 mL) was slowly added sodium hydride (60%, oily, 2.4 g) at 0° C., and the mixture was stirred at room temperature for 30 min. Benzylbromide (7.1 mL) was slowly added to the reaction mixture, and the mixture was stirred overnight at room temperature. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography to give 1-benzyl-2-methyl-1H-imidazole-4-carbaldehyde (3.8 g, yield 38%) as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). melting point 61° C.

Workup

  1. customat 0° C.
  2. stirringthe mixture was stirred overnight at room temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ace65b178b9f4ba497042e3d5c36f4b5
Source dataset
uspto-grants-2013_07
Patent number
US08492405B2

Reaction notes

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