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Water → N-[3-Fluoro-4-(phenylsulfonyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2methylpropanamide

HRID 865758
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 865758
[F:1][C:2]([F:10])([F:9])[C:3]([OH:8])([CH3:7])[C:4](O)=[O:5].S(Cl)(Cl)=O.[F:15][C:16]1[CH:17]=[C:18]([NH2:31])[CH:19]=[CH:20][C:21]=1[S:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:24])=[O:23].O>CN(C)C(=O)C>[F:15][C:16]1[CH:17]=[C:18]([NH:31][C:4](=[O:5])[C:3]([OH:8])([CH3:7])[C:2]([F:10])([F:9])[F:1])[CH:19]=[CH:20][C:21]=1[S:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:24])=[O:23]
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Komponenten

6

Edukt 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 27751253,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acidHCID 107532343-Fluoro-4-(phenyl sulfonyl)benzeneamine

Produkt 1

HCID 10834289N-[3-Fluoro-4-(phenylsulfonyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2methylpropanamideAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

To a stirred, cooled (-20° C.) solution of 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid (0.71 g, 4.5 mmol) in N,N-dimethylacetamide (10 mL) was added thionyl chloride (0.54 g, 4.5 mmol) and the mixture stirred at -10° to -15° C. for 1 hour. 3-Fluoro-4-(phenyl sulfonyl)benzeneamine (0.75 g, 3.0 mmol) was added in one portion and the reaction mixture stirred at room temperature overnight. The mixture was poured into water and the aqueous solution filtered through Celite. The Celite was washed with methylene chloride (75 mL), the organic extract dried (MgSO4) and concentrated in vacuo to a tan solid. Purification by flash column chromatography (5% v/v ethyl acetate/methylene chloride) yielded the title propanamide as a white solid (0.79 g, 68%); mp 147°-149° C. 1H-NMR (250 MHz, d6-DMSO): 1.58 (s, 3H, CH3) 7.65-7.69 (m, 4H, aromatic+OH) 7.74 (d, 1H, J=7.2 Hz, aromatic) 7.83-7.94 (m, 3H, aromatic) 8.02 (t, 1H, J=8.3 Hz, aromatic) 10.61 (s, 1H, NH). MS (CI, CH4): 392 (M+1).

Aufarbeitung

  1. stirringthe reaction mixture stirred at room temperature overnight
  2. filtrationthe aqueous solution filtered through Celite
  3. washThe Celite was washed with methylene chloride (75 mL)
  4. extractionthe organic extract
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo to a tan solid
  7. customPurification by flash column chromatography (5% v/v ethyl acetate/methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-eab19f6c3c3649bdb1e4e9aa27574b8d
Quelldatensatz
uspto-grants-1996_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05567735

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