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

HRID 1077825Notes

Reaction equation

HRID 1077825 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[CH:5][N:4]=[C:3]1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1.C=O.[C:20]([O-])(=[O:22])C.[Na+].[OH-].[Na+]>C(O)(=O)C>[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([CH2:20][OH:22])[N:4]=[C:3]1[C:8]1[CH:9]=[CH:10][C:11]([C:14]([F:16])([F:17])[F:15])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 194303261,5-Dimethyl-2-(4-trifluoromethylphenyl)imidazole

Product 1

HCID 194302591,5-Dimethyl-4-hydroxymethyl-2-(4-trifluoromethylphenyl)imidazoleYield 59.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1,5-dimethyl-2-(4-trifluoromethylphenyl)imidazole (0.6 g), aqueous formaldehyde (3.5 ml of 36%), sodium acetate (0.6 g), and acetic acid (0.5 ml) was refluxed for 24 hours. The mixture was cooled, and concentrated sodium hydroxide added until the mixture was just basic, keeping the temperature at about 10° C. The mixture was extracted with methylene chloride, and solvent removed from the organic layer under reduced pressure. The residue was flash-chromatographed on silica gel, eluting with methylene chloride containing methanol (97/3), to yield 0.4 g of 1,5-dimethyl-4-hydroxymethyl-2-(4-trifluoromethyl-phenyl)imidazole, m.p. 152° C.

Workup

  1. temperaturewas refluxed for 24 hours
  2. temperatureThe mixture was cooled
  3. customat about 10° C
  4. extractionThe mixture was extracted with methylene chloride, and solvent
  5. customremoved from the organic layer under reduced pressure
  6. customThe residue was flash-chromatographed on silica gel
  7. washeluting with methylene chloride
  8. additioncontaining methanol (97/3)

Sources & evidence

ORD record
ord-6f736e4566c7406da369b152bec07a1e
Source dataset
uspto-grants-1996_08
Patent number
US05545645

Reaction notes

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