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

HRID 1690146
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1690146
[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].OO.[OH2:46].C[OH:48]>[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:48])=[O:46])=[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]
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Komponenten

6

Edukt 4

HCID 784Hydrogen PeroxideHCID 887MethanolHCID 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

Produkt 1

HCID 592009843-(3-(4-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)-2-propylphenoxy)benzyl)-5-methyl-5-(6-(methylsulfonyl)pyridin-3-yl)imidazolidine-2,4-dione
Ausbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 10269745Tantalum chlorideKatalysator

Versuchsvorschrift

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 methanol (640 μL), tantalum chloride (0.6 mg, 0.00159 mmol) and 30% hydrogen peroxide solution (71 μL, 0.07967 mmol) 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 2 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 (11.3 mg, yield >99%) was obtained as a yellow oil.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-3811f927398c4815ac3a2bf7cc0a7a97
Quelldatensatz
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08153634B2

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