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

HRID 52346

Reaction equation

HRID 52346 reaction equation
[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)[CH2:10][C:11](O)([C:13]([F:16])([F:15])[F:14])[N:12]=2)=[CH:4][N:3]=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:16])[F:14])[N:12]=2)=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 229981692-Methyl-5-[4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1h-imidazol-2-yl]pyridine

Product 1

HCID 101778455-[1-(4-Methanesulfonyl-phenyl)-4-trifluoromethyl-1H-imidazol-2-yl]-2-methyl-pyridineYield 66%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of the 4,5-dihydro-imidazole of step 2 (6.2 g, 15.5 mmol) and p-toluenesulfonic acid monohydrate (1.6 g, 8.4 mmol) in toluene (550 ml) was heated to reflux for 24 hours. The reaction mixture was cooled and the solvent removed under reduced pressure. The crude mixture (8.2 g) was chromatographed on silica gel using ethyl acetate/acetone (98/2) to give pure 2-methyl-5-[1-[4-(methylsulfonyl)phenyl]-4-trifluoromethyl-1H-imidazol-2-yl]pyridine (3.9 g, 66%) as a white solid: mp (DSC) 163° C. Anal Calc'd. for C17H14N3SO2F3 : C, 53.54, H, 3.70, N, 11.02, S, 8.41. Found: C, 53.12, H, 3.56, N, 11.00, S, 8.50.

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 (8.2 g) was chromatographed on silica gel

Sources & evidence

ORD record
ord-f6a86c8446f94b969f55ff40707192d9
Source dataset
uspto-grants-1997_04
Patent number
US05616601

Linked notes

Loading…