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

HRID 1166349Notes

Reaction equation

HRID 1166349 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

Conditions

Temperature
72.5 °C

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. customthe solvent is removed
  3. dissolutionThe residue is redissolved in methylene chloride
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product is purified by chromatography (silica gel, toluene/ethyl acetate, 7/3)

Sources & evidence

ORD record
ord-dc769f19af07430e86814771b8a739ac
Source dataset
uspto-grants-2003_09
Patent number
US06613789B2

Reaction notes

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