p-Toluenesulfonic acid monohydrate → 5-methyl-2-[1-[4-(methylsulfonyl)phenyl]-4-trifluoromethyl-1H-imidazol-2-yl]pyridine

HRID 52352Notes

Reaction equation

HRID 52352 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[N:9]([C:18]3[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=3)[CH2:10][C:11](O)([C:13]([F:16])([F:15])[F:14])[N:12]=2)=[CH:6][CH:7]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:18]3[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=3)[CH:10]=[C:11]([C:13]([F:15])([F:14])[F:16])[N:12]=2)=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 199633603-methyl-6-[4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1H-imidazol-2-yl]pyridine

Product 1

HCID 108098545-methyl-2-[1-[4-(methylsulfonyl)phenyl]-4-trifluoromethyl-1H-imidazol-2-yl]pyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of the 4,5-dihydro-imidazole of step 2 (10 mmol) and p-toluenesulfonic acid monohydrate (2 mmol) in toluene (200 ml) is heated to reflux for 24 hours. The reaction mixture is cooled and the solvent removed under reduced pressure. The crude mixture is chromatographed on silica gel using mixtures of ethyl acetate and acetone as eluants to give the desired product.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 24 hours
  3. temperatureThe reaction mixture is cooled
  4. customthe solvent removed under reduced pressure
  5. customThe crude mixture is chromatographed on silica gel using mixtures of ethyl acetate and acetone as eluants

Sources & evidence

ORD record
ord-51e4937b69ca4e239267b0e2768a42e7
Source dataset
uspto-grants-1997_04
Patent number
US05616601

Reaction notes

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