p-Toluenesulfonic acid monohydrate → Pyridine,2-methyl-3-[1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-1h-imidazol-2-yl]-

HRID 1352998Notes

Reaction equation

HRID 1352998 reaction equation
[CH3:1][C:2]1[C:7]([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:5]=[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[C:7]([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:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 22998070HCID 22998070, compound

Product 1

HCID 10786069Pyridine,2-methyl-3-[1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-1h-imidazol-2-yl]-Yield 73.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-methyl-3-[4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1H-imidazol-2-yl]pyridine from step 3 (3.97 g, 0.01 mol) and p-toluenesulfonic acid monohydrate (0.60 g, 0.0032 mol) in 250 mL of toluene was heated to reflux for 24 hours. The reaction mixture was cooled and the solvent was removed under reduced pressure. The residue was partitioned between water and methylene chloride. The organic layer was washed with water, saturated sodium bicarbonate solution and brine, dried over magnesium sulfate and filtered. The filtrate was evaporated in vacuo and the crude product was purified by recrystallization from ethyl acetate/hexane to give 2.8 g of 2-methyl-3-[1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]pyridine (73%): mp 160–161° C. Anal. Calc'd. for C17H14F3N3O2S: C, 53.54, H, 3.70, N, 11.02, S, 8.41. Found: C, 53.58, Ho 3.88, N, 11.02, S, 8.51.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 24 hours
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was partitioned between water and methylene chloride
  6. washThe organic layer was washed with water, saturated sodium bicarbonate solution and brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customThe filtrate was evaporated in vacuo
  10. customthe crude product was purified by recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-f9f8f1f7ea5d4aaa8171da62bbe48244
Source dataset
uspto-grants-2007_05
Patent number
US07220770B2

Reaction notes

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