Imidazole → 4-(1H-imidazol-1-yl)benzaldehyde

HRID 856043Notes

Reaction equation

HRID 856043 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[NH:10]1[CH:14]=[CH:13][N:12]=[CH:11]1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CS(C)=O>[N:10]1([C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH:14]=[CH:13][N:12]=[CH:11]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 680234-Fluorobenzaldehyde

Product 1

HCID 7365304-(1H-imidazol-1-yl)benzaldehydeYield 34%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4-fluorobenzaldehyde (4.96 g, 40 mmol), imidazole (2.86 g, 42 mmol), and potassium carbonate (6.08 g, 44 mmol) in DMSO (40 ml) was stirred at 110° C. overnight. The reaction mixture was allowed to return to room temperature, and poured into ice water (100 ml). The resulting precipitates were collected by filtration and washed with water and then with ethyl acetate to afford 4-(imidazol-1-yl)benzaldehyde (2.33 g, yield 34%) as a pale yellow crystalline powder.

Workup

  1. customto return to room temperature
  2. customThe resulting precipitates
  3. filtrationwere collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-08182df049dc477da6d6feee0f8d93f1
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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