1,5-Dimethyl-4-hydroxymethyl-2-(4-trifluoromethylphenyl)imidazole → 1,5-Dimethyl-4-formyl-2-(4-trifluoromethylphenyl)imidazole

HRID 22244Notes

Reaction equation

HRID 22244 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([CH2:8][OH:9])[N:4]=[C:3]1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([CH:8]=[O:9])[N:4]=[C:3]1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:18])([F:19])[F:17])=[CH:12][CH:11]=1

Participants

4

Reactant 1

HCID 194302591,5-Dimethyl-4-hydroxymethyl-2-(4-trifluoromethylphenyl)imidazole

Product 1

HCID 152882331,5-Dimethyl-4-formyl-2-(4-trifluoromethylphenyl)imidazoleYield 100.8%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6212ChloroformSolvent

Procedure

A mixture of 1,5-dimethyl-4-hydroxymethyl-2-(4-trifluoromethylphenyl)imidazole (0.5 g) and manganese dioxide (2 g) in 20 ml of chloroform was refluxed for 24 hours. A further 2 g of manganese dioxide was added, and the mixture refluxed for a further 3 hours. The mixture was cooled, the solid material filtered off, and washed with methylene chloride. The solvent was removed from the filtrate under reduced pressure, to yield 0.5 g of 1,5-dimethyl-4-formyl-2-(4-trifluoromethylphenyl)imidazole, m.p. 144° C.

Workup

  1. temperaturewas refluxed for 24 hours
  2. temperaturethe mixture refluxed for a further 3 hours
  3. temperatureThe mixture was cooled
  4. filtrationthe solid material filtered off
  5. washwashed with methylene chloride
  6. customThe solvent was removed from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-4a4be547aa55439685a4cbd4c667d15f
Source dataset
uspto-grants-1995_06
Patent number
US05428037

Reaction notes

Loading…