HCID 23444980, compound → 1-(3,4-dichloro-phenyl)-1H-imidazole-4-carbaldehyde

HRID 1841220Notes

Reaction equation

HRID 1841220 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[C:12]([CH2:14][OH:15])[N:11]=[CH:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]>C1COCC1.O.[O-2].[Mn+4].[O-2]>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[C:12]([CH:14]=[O:15])[N:11]=[CH:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 1

HCID 23444980HCID 23444980, compound

Product 1

HCID 234451021-(3,4-dichloro-phenyl)-1H-imidazole-4-carbaldehydeYield 25%

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of [1-(3,4-dichloro-phenyl)-1H-imidazol-4-yl]-methanol (10.8 g, 44.3 mmol) in a mixture of THF (270 ml) and H2O (30 ml) was treated with manganese(IV) oxide (5 g, 57.5 mmol) and the mixture was refluxed for 4 h. A second portion of manganese(IV) oxide (1.5 g) was added and reflux continued for 1.5 h. The mixture was filtered over Celite, and the residue was washed with MeOH. Toluene was added to the filtrate, and the H2O was removed azeotropically. The brown residue was taken up in CH2Cl2 and upon standing white crystals formed. Filtration afforded 1-(3,4-dichloro-phenyl)-1H-imidazole-4-carbaldehyde (2.5 g, 25%). MS: m/e=240.0 (M+).

Workup

  1. temperaturethe mixture was refluxed for 4 h
  2. temperaturereflux
  3. filtrationThe mixture was filtered over Celite
  4. washthe residue was washed with MeOH
  5. additionToluene was added to the filtrate
  6. customthe H2O was removed azeotropically
  7. customformed
  8. filtrationFiltration

Sources & evidence

ORD record
ord-555c1100d0424bd1a0fc8674633e1023
Source dataset
uspto-grants-2004_01
Patent number
US06683097B2

Reaction notes

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