Sodium Acetate → {[2,6-Difluoro-4-(5-methyl-3-phenylisoxazol-4-yl)phenyl]thio}methyl acetate

HRID 47653Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 47653
[F:1][C:2]1[CH:3]=[C:4]([C:13]2[C:14]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:15][O:16][C:17]=2[CH3:18])[CH:5]=[C:6]([F:12])[C:7]=1[S:8]([CH3:11])(=O)=O.[C:25]([O-:28])(=[O:27])[CH3:26].[Na+]>C(OC(=O)C)(=O)C>[C:25]([O:28][CH2:11][S:8][C:7]1[C:2]([F:1])=[CH:3][C:4]([C:13]2[C:14]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:15][O:16][C:17]=2[CH3:18])=[CH:5][C:6]=1[F:12])(=[O:27])[CH3:26]

Komponenten

4

Edukt 2

HCID 517045Sodium AcetateHCID 99244894-[3,5-Difluoro-4-(methylsulfonyl)-phenyl]-5-methyl-3-phenylisoxazole

Produkt 1

HCID 22746414{[2,6-Difluoro-4-(5-methyl-3-phenylisoxazol-4-yl)phenyl]thio}methyl acetateAusbeute 82,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7918Acetic AnhydrideLösungsmittel

Versuchsvorschrift

A slurry of 4-[3,5-difluoro-4-(methylsulfinyl)phenyl]-5-methyl-3-phenylisoxazole (2.3 g, 6.8 mmol) (step 9 example 14), sodium acetate (3.4 g, 41 mmol) in acetic anhydride (30 mL) was heated and held at reflux for 9 hours. The mixture was concentrated on at reduced pressure and the residue was treated with dilute aqueous sodium bicarbonate and extracted with dichloromethane (1×200 mL, 2×75 mL). The combined extracts were washed with dilute sodium bicarbonate, dilute ammonium chloride, dried with magnesium sulfate and concentrated. The product was purified by silica gel chromatography using 1% ethyl acetate/50% dichloromethane in hexanes to give {[2,6-difluoro-4-(5-methyl-3-phenylisoxazol-4-yl)phenyl]thio}methyl acetate as a white solid (2.1 g, 82%), MP 130.3-130.3° C. 1H NMR (CDCl3/400 MHz) 7.34-7.43 (m, 5H), 6.73-6.79 (m, 2H), 5.29 (s, 2H), 2.49 (s, 3H) 2.05 (s, 3H). HRMS m/z 376.0822 (M+H+, Calcd 376.0819). Anal. Calcd for C19H15F2NO3S: C, 60.79; H, 4.03; N, 3.73. Found: C, 60.44; H, 4.09; N, 3.66.

Aufarbeitung

  1. temperatureat reflux for 9 hours
  2. concentrationThe mixture was concentrated on at reduced pressure
  3. additionthe residue was treated with dilute aqueous sodium bicarbonate
  4. extractionextracted with dichloromethane (1×200 mL, 2×75 mL)
  5. washThe combined extracts were washed with dilute sodium bicarbonate, dilute ammonium chloride
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated
  8. customThe product was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f7ec55890ea84a82a5138f0d756bb2f4
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699884B2

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