p-Toluenesulfonic acid monohydrate → HCID 22316646, compound

HRID 2086696Notes

Reaction equation

HRID 2086696 reaction equation
[Br: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])=[C:20]([F:28])[CH:19]=3)[CH2:10][C:11](O)([C:13]([F:16])([F:15])[F:14])[N:12]=2)=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br: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:25])=[O:26])=[C:20]([F:28])[CH:19]=3)[CH:10]=[C:11]([C:13]([F:15])([F:14])[F:16])[N:12]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 22316735HCID 22316735, compound

Product 1

HCID 22316646HCID 22316646, compoundYield 51.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-(4-bromophenyl)-1-[3-fluoro-4-(methylsulfonyl)phenyl]-4-hydroxy-4-trifluoromethyl-4,5-dihydro-1H-imidazole (3.05 g, 6.33 mmol) and p-toluenesulfonic acid monohydrate (0.300 g) in toluene (250 mL) was heated to reflux for 21 hours. The reaction mixture was cooled and the solvent removed under reduced pressure. The crude residue was redissolved in methylene chloride (150 mL) and the whole washed with water, aqueous NaHCO3 (50 mL), and brine. After dried over MgSO4, and concentrated in vacuo. The crude mixture was purified by flash chromatography eluting with hexane/ethyl acetate (3/1) to give the subtitle compound (1.517 g, 51.8% yield).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 21 hours
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent removed under reduced pressure
  5. dissolutionThe crude residue was redissolved in methylene chloride (150 mL)
  6. washthe whole washed with water, aqueous NaHCO3 (50 mL), and brine
  7. dry with materialAfter dried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe crude mixture was purified by flash chromatography
  10. washeluting with hexane/ethyl acetate (3/1)

Sources & evidence

ORD record
ord-7772bb554590409894f46e3751dba5d7
Source dataset
uspto-grants-2004_04
Patent number
US06727238B2

Reaction notes

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