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

HRID 52344Notes

Reaction equation

HRID 52344 reaction equation
O[C:2]1([C:23]([F:26])([F:25])[F:24])[CH2:6][N:5]([C:7]2[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=2)[C:4]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[N:3]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:16][S:13]([C:10]1[CH:9]=[CH:8][C:7]([N:5]2[CH:6]=[C:2]([C:23]([F:25])([F:26])[F:24])[N:3]=[C:4]2[C:17]2[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=2)=[CH:12][CH:11]=1)(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 229977844-(4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1H-imidazol-2-yl]pyridine

Product 1

HCID 105709704-[1-(4-Methanesulfonyl-phenyl)-4-trifluoromethyl-1H-imidazol-2-yl]-pyridineYield 41%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of the 4,5-dihydro-imidazole of step 2 (0.85 g, 2.2 mmol) and p-toluenesulfonic acid monohydrate (0.12 g) in toluene (150 ml) was heated to reflux for 24 hours. The reaction mixture was cooled and the solvent removed under reduced pressure. The crude mixture was chromatographed on silica gel using ethyl acetate/acetone (96/4) to give pure 4-[1-[4-(methylsulfonyl)phenyl]-4-trifluoromethyl-1H-imidazol-2-yl]pyridine (330 mg, 41%) as a white solid: mp (DSC) 197° C. Anal. Calc'd. for C16H12N3SO2F3 : C, 52.30, H, 3.29, N, 11.44, S, 8.73. Found C, 52.19, H, 3.26, N, 11.25, S, 8.99.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 24 hours
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent removed under reduced pressure
  5. customThe crude mixture was chromatographed on silica gel

Sources & evidence

ORD record
ord-b3be9a4260b54aa2a737de86e8b2503d
Source dataset
uspto-grants-1997_04
Patent number
US05616601

Reaction notes

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