Hydrogen Peroxide → 3-(3-(4-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)-2-propylphenoxy)benzyl)-5-methyl-5-(6-(methylsulfinyl)pyridin-3-yl)imidazolidine-2,4-dione

HRID 1690145Notes

Reaction equation

HRID 1690145 reaction equation
[F:1][C:2]([F:43])([F:42])[C:3]([C:9]1[CH:38]=[CH:37][C:12]([O:13][C:14]2[CH:15]=[C:16]([CH:34]=[CH:35][CH:36]=2)[CH2:17][N:18]2[C:22](=[O:23])[C:21]([CH3:32])([C:24]3[CH:25]=[N:26][C:27]([S:30][CH3:31])=[CH:28][CH:29]=3)[NH:20][C:19]2=[O:33])=[C:11]([CH2:39][CH2:40][CH3:41])[CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].[OH:44]O.O>C(#N)C.[Cl-].[Ta+5].[Cl-].[Cl-].[Cl-].[Cl-]>[F:5][C:4]([F:7])([F:6])[C:3]([C:9]1[CH:38]=[CH:37][C:12]([O:13][C:14]2[CH:15]=[C:16]([CH:34]=[CH:35][CH:36]=2)[CH2:17][N:18]2[C:22](=[O:23])[C:21]([CH3:32])([C:24]3[CH:25]=[N:26][C:27]([S:30]([CH3:31])=[O:44])=[CH:28][CH:29]=3)[NH:20][C:19]2=[O:33])=[C:11]([CH2:39][CH2:40][CH3:41])[CH:10]=1)([OH:8])[C:2]([F:1])([F:42])[F:43]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 962WaterHCID 592010673-(3-(4-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)-2-propylphenoxy)benzyl)-5-methyl-5-(6-(methylthio)pyridin-3-yl) imidazolidine-2,4-dione

Product 1

HCID 592011583-(3-(4-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)-2-propylphenoxy)benzyl)-5-methyl-5-(6-(methylsulfinyl)pyridin-3-yl)imidazolidine-2,4-dioneYield 70%

Reagents, catalysts & solvents 2

HCID 10269745Einecs 254-460-4CatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-(3-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-propylphenoxy)benzyl)-5-methyl-5-(6-(methylthio)pyridin-3-yl) imidazolidine-2,4-dione (10 mg, 0.0159 mmol) in acetonitrile (640 tantalum chloride (0.6 mg, 0.00159 mmol) and 30% hydrogen peroxide solution (71 μL) were added under ice-cold conditions, and the resultant mixture was stirred under ice-cold conditions for 1 hour and then stirred at room temperature for 9 hours. The reaction solution was added with water and extracted with ethyl acetate. The organic layer was washed with brine, dried using anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified using silica-gel column chromatography (ethyl acetate) and the title compound (7.2 mg, yield 70%) was obtained as a yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe obtained residue was purified

Sources & evidence

ORD record
ord-131d573279d448deb382c9e6e392e55b
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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