Methanol → 4-Phenyl-5-(4-methylsulfonylphenyl)-alpha,alpha-bis(trifluoromethyl)-1H-imidazole-2-methanol

HRID 482915Notes

Reaction equation

HRID 482915 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:20]([C:26]([F:29])([F:28])[F:27])([C:22]([F:25])([F:24])[F:23])[OH:21])[NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][C:15](SC)=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O[O:31][S:32]([O-:34])=O.[K+].[CH3:36]O>>[C:12]1([C:11]2[N:10]=[C:9]([C:20]([C:22]([F:24])([F:25])[F:23])([C:26]([F:27])([F:28])[F:29])[OH:21])[NH:8][C:7]=2[C:1]2[CH:6]=[CH:5][C:4]([S:32]([CH3:36])(=[O:34])=[O:31])=[CH:3][CH:2]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 13580030HCID 13580030, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 135800314-Phenyl-5-(4-methylsulfonylphenyl)-alpha,alpha-bis(trifluoromethyl)-1H-imidazole-2-methanol

Procedure

A mixture of 4.0 g (9.25 mmoles) of 4-phenyl-5-(4-methylthiophenyl)-α,α-bis(trifluoromethyl)-1H-imidazole-2-methanol, 14.2 g (23.1 mmoles) of Oxone® and 115 ml of methanol were stirred overnight. The inorganic solid was filtered off, and the filtrate was concentrated to dryness. The residue was partitioned between ethyl acetate and water and the organic layer was separated. The organic layer was washed with brine and water, dried over anhydrous magnesium sulfate and concentrated in vacuo. The product was recrystallized from a mixture of dichloroethane and butyl chloride affording 2.89 g (67%) of the title compound as a white solid, m.p. 223°-225°.

Workup

  1. filtrationThe inorganic solid was filtered off
  2. concentrationthe filtrate was concentrated to dryness
  3. customThe residue was partitioned between ethyl acetate and water
  4. customthe organic layer was separated
  5. washThe organic layer was washed with brine and water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe product was recrystallized from a mixture of dichloroethane and butyl chloride affording 2.89 g (67%) of the title compound as a white solid, m.p. 223°-225°

Sources & evidence

ORD record
ord-be28d067ba3b447d8427fe9bec9e17d5
Source dataset
uspto-grants-1986_03
Patent number
US04576958

Reaction notes

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