p-Toluenesulfonic acid monohydrate → 1-(4-Methanesulfonyl-phenyl)-2-thiophen-2-yl-4-trifluoromethyl-1H-imidazole

HRID 1166378Notes

Reaction equation

HRID 1166378 reaction equation
O[C:2]1([C:22]([F:25])([F:24])[F:23])[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[S:18][CH:19]=[CH:20][CH:21]=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:22]([F:25])([F:24])[F:23])[N:3]=[C:4]2[C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)=[CH:12][CH:11]=1)(=[O:14])=[O:15]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 229979092-[4-Hydroxy-1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1h-imidazol-2-yl]thiophene

Product 1

HCID 117936321-(4-Methanesulfonyl-phenyl)-2-thiophen-2-yl-4-trifluoromethyl-1H-imidazoleYield 82%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of the 4,5-dihydro-imidazole of step 2 (0.60 g, 1.54 mmol) and p-toluenesulfonic acid monohydrate (0.12 g, 0.63 mmol) in toluene (100 ml) was heated to reflux for 4.5 hours. The reaction mixture was cooled and the solvent removed under reduced pressure. The crude mixture (1.2 g) was purified by chromatography on silica gel using ethyl acetate/hexane 50/50 to give pure 2-[1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]thiophene (0.47 g, 82%) as a white solid: mp (DSC) 182° C. Anal. Calc'd. for C15H11N2S2O2F3 C, 48.38, H, 2.98, N, 7.52, S, 17.22. Found: C, 48.36, H, 3.02, N, 7.42, S, 17.47.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4.5 hours
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent removed under reduced pressure
  5. customThe crude mixture (1.2 g) was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-7e5cc1d938654f6c8d33455f31661d6f
Source dataset
uspto-grants-2003_09
Patent number
US06613789B2

Reaction notes

Loading…