Methanol → 1-[2-(4-chlorophenyl)-1-[4-(methylsulfonyl)phenyl]-1H-imidazol-4-yl]-1-ethanone

HRID 1166399Notes

Reaction equation

HRID 1166399 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:22]3[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][CH:23]=3)[CH:10]=[C:11]([CH2:13][O:14]C3C=CC(C)=CC=3)[N:12]=2)=[CH:4][CH:3]=1.[CH3:32]O>[OH-].[Na+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([C:22]3[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][CH:23]=3)[CH:10]=[C:11]([C:13](=[O:14])[CH3:32])[N:12]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 229977132-(4-chlorophenyl)-4-[(4-methylphenoxy)methyl]-1-[4-(methylsulfonyl)phenyl]-1H-imidazole

Product 1

HCID 229977331-[2-(4-chlorophenyl)-1-[4-(methylsulfonyl)phenyl]-1H-imidazol-4-yl]-1-ethanone

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A suspension of ethyl [2-(4-chlorophenyl)-1-[4-(methylsulfonyl)phenyl]-1H-imidazol-4-yl] carboxylate (Example 159) (929 mg, 2.29 mmol) in 16 ml of methanol and 16 ml of 1N aqueous sodium hydroxide was stirred at reflux for one hour. After cooling, the mixture was concentrated, water was added, and the resulting mixture was acidified with acetic acid. The mixture was extracted with dichloromethane, and the combined organic extracts were dried over sodium sulfate, filtered, and evaporated. Acetic acid was removed by azeotropic distillation with toluene to give the title compound, 520 mg, as a white crystalline solid: mp (DSC) 121° C. Anal. Calc'd. for C17H13ClN2O4S.H2O (MW 394.83): C, 51.71; H, 3.32; N, 7.10. Found: C, 51.89; H, 3.29; N, 6.97.

Workup

  1. temperatureat reflux for one hour
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated
  4. additionwater was added
  5. extractionThe mixture was extracted with dichloromethane
  6. dry with materialthe combined organic extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customAcetic acid was removed by azeotropic distillation with toluene

Sources & evidence

ORD record
ord-a4c2285050f246bcbcc8cb7092468c68
Source dataset
uspto-grants-2003_09
Patent number
US06613789B2

Reaction notes

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