p-Toluenesulfonic acid monohydrate → 1-(4-Methanesulfonyl-phenyl)-2-thiophen-3-yl-4-trifluoromethyl-1H-imidazole

HRID 52362Notes

Reaction equation

HRID 52362 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[CH:21]=[CH:20][S: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:22]([F:24])([F:25])[F:23])[N:3]=[C:4]2[C:17]2[CH:21]=[CH:20][S:19][CH:18]=2)=[CH:12][CH:11]=1)(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrate2×HCID 22998113HCID 22998113, compound

Product 1

HCID 106192741-(4-Methanesulfonyl-phenyl)-2-thiophen-3-yl-4-trifluoromethyl-1H-imidazoleYield 64%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of the 4,5-dihydro-imidazole of step 2 (1.5 g, 3.8 mmol) and p-toluenesulfonic acid monohydrate (0.30 g, 1.5 mmol) in toluene (250 ml) was heated to reflux for 40 hours. An additional p-toluenesulfonic acid monohydrate (0.15 g, 0.78 mmol) was added. The reaction mixture was heated to reflux for 18 hours. The reaction mixture was cooled and the solvent removed under reduced pressure. The crude mixture (3.5 g) was chromatographed on silica gel using ethyl acetate/toluene (55/45) to give pure 3-[1-[4-(methylsulfonyl)phenyl]-4-(trifluoromethyl)-1H-imidazol-2-yl]thiophene (0.90 g, 64%) as a white solid: mp 194°-197° C. Anal. Calc'd. for C15H11N2S2O2F3 : C, 48.38, H, 2.98, N, 7.52, S, 17.22. Found C, 48.74, H, 2.98, N, 7.56, S, 17.45.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 40 hours
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux for 18 hours
  5. temperatureThe reaction mixture was cooled
  6. customthe solvent removed under reduced pressure
  7. customThe crude mixture (3.5 g) was chromatographed on silica gel

Sources & evidence

ORD record
ord-ab6a3aa5b14b4127be31352bc1dd8c69
Source dataset
uspto-grants-1997_04
Patent number
US05616601

Reaction notes

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