3-Bromo-1,1,1-trifluoro-2-propanone → HCID 22997716, compound

HRID 1352962Notes

Reaction equation

HRID 1352962 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:8]=[CH:7][C:6]([C:9](=[NH:21])[NH:10][C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.C(=O)(O)[O-].[Na+].Br[CH2:30][C:31](=[O:36])[C:32]([F:35])([F:34])[F:33]>C(O)(C)C>[OH:36][C:31]1([C:32]([F:35])([F:34])[F:33])[CH2:30][N:10]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)[C:9]([C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:22])[F:23])=[CH:8][CH:7]=2)=[N:21]1

Participants

5

Reactant 3

HCID 790083-Bromo-1,1,1-trifluoro-2-propanoneHCID 516892Sodium BicarbonateHCID 178504795HCID 178504795, compound

Product 1

HCID 22997716HCID 22997716, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a mixture of 4-(trifluoromethyl)-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide (10 mmol) and sodium bicarbonate (20 mmol) in isopropanol (100 mL), 3-bromo-1,1,1-trifluoroacetone (20 mmol) is added. After heating the reaction mixture at 70–75° C. for 20 hours, the solvent is removed. The residue is redissolved in methylene chloride and washed with water. The organic fractions are combined, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product is purified by chromatography (silica gel, toluene/ethyl acetate, 7/3) to give 4-hydroxy-1-[4-(methylsulfonyl)phenyl]-2-(4-trifluoromethylphenyl)-4-trifluoromethyl-4,5-dihydro-1H-imidazole.

Workup

  1. additionis added
  2. temperatureAfter heating the reaction mixture at 70–75° C. for 20 hours
  3. customthe solvent is removed
  4. dissolutionThe residue is redissolved in methylene chloride
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product is purified by chromatography (silica gel, toluene/ethyl acetate, 7/3)

Sources & evidence

ORD record
ord-e0382e326247466dae0aad216969f26c
Source dataset
uspto-grants-2007_05
Patent number
US07220770B2

Reaction notes

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