p-Toluenesulfonic acid monohydrate → HCID 15908406, compound

HRID 497191Notes

Reaction equation

HRID 497191 reaction equation
O[C:2]1([C:28]([F:31])([F:30])[F:29])[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][C:20]([C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)=[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:28]([F:30])([F:29])[F:31])[N:3]=[C:4]2[C:17]2[CH:22]=[CH:21][C:20]([C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)(=[O:14])=[O:15]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 22316766HCID 22316766, compound

Product 1

HCID 15908406HCID 15908406, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-hydroxy-1-[4-(methylsulfonyl)phenyl]-2-[4-(2-thienyl)phenyl]-4-(trifluoromethyl)-4,5-dihydro-1H-imidazole (0.345 g, 0.74 mmol) and p-toluenesulfonic acid monohydrate (0.035 g) in toluene (40 mL) was heated to reflux for 7 hours. The reaction mixture was cooled and the solvent removed under reduced pressure. The crude residue was redissolved in CH2Cl2 (50 mL) and the whole washed with water, aqueous NaHCO3 (30 mL), and brine. After dried over Na2SO4, and concentration in vacuo. The crude mixture was purified by flash chromatography eluting with hexane/ethyl acetate (2/1). The resulting solid was recrystallized from ethyl acetate-hexane to give the title compound (0.212 g, 63.9% yield).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 7 hours
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent removed under reduced pressure
  5. dissolutionThe crude residue was redissolved in CH2Cl2 (50 mL)
  6. washthe whole washed with water, aqueous NaHCO3 (30 mL), and brine
  7. dry with materialAfter dried over Na2SO4, and concentration in vacuo
  8. customThe crude mixture was purified by flash chromatography
  9. washeluting with hexane/ethyl acetate (2/1)
  10. customThe resulting solid was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-11c4fb6dac574a1fad22dbe283571814
Source dataset
uspto-grants-2005_09
Patent number
US06949536B2

Reaction notes

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