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

HRID 722466Notes

Reaction equation

HRID 722466 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+]>CN(C=O)C>[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

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 680234-Fluorobenzaldehyde

Product 1

HCID 7365304-(1H-imidazol-1-yl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 20 g (161.1 mmol) of p-fluorobenzaldehyde in 300 ml of DMF, 19.8 g (290.8 mmol) of imidazole and 44.5 g (322.24 mmol) of potasium carbonate are step by step added at r.t. After being stirred for 5.5 h at 100° C., the reaction mixture is cooled to r.t., diluted with ice water and then the mixture is extracted with AcOEt and CH2Cl2. The combined extracts are concentrated under reduced pressure to give 4-imidazol-1-yl-benzaldehyde as a pale yellow powder. 1H-NMR (400 MHz, CDCl3): 7.26 (s, 1H), 7.38 (2, 1H), 7.59 (d, 2H, J=8.56 Hz), 7.98 (s, 1H), 8.02 (d, 2H, J=8.56 Hz), 10.05 (s, 1H).

Workup

  1. additionadded at r.t
  2. temperaturethe reaction mixture is cooled to r.t.
  3. extractionthe mixture is extracted with AcOEt and CH2Cl2
  4. concentrationThe combined extracts are concentrated under reduced pressure

Sources & evidence

ORD record
ord-ce5719ff673f4aa2894a8244c5150988
Source dataset
uspto-grants-2006_11
Patent number
US07138432B1

Reaction notes

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