Potassium Carbonate → HCID 86744603, Verbindung

HRID 981465

Reaktionsgleichung

Reaktionsgleichung von HRID 981465
[SH:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[C:11](=[O:14])([O-])[O-].[K+].[K+].CO[C:19]1[CH:24]=[CH:23][C:22]([CH:25]2[O:27][CH:26]2[C:28]([NH2:30])=[O:29])=[CH:21][CH:20]=1>C(#N)C>[OH:27][CH:26]([CH:25]([S:1][CH2:2][C:3](=[O:4])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:22]1[CH:23]=[CH:24][CH:19]=[CH:20][C:21]=1[C:5]1[CH:10]=[CH:9][C:8]([O:14][CH3:11])=[CH:7][CH:6]=1)[C:28]([NH2:30])=[O:29]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 110736092-Mercapto-1-phenylethanoneHCID 148559763-(4-Methoxyphenyl)oxiranecarboxamide

Produkt 1

HCID 86744603HCID 86744603, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 8.0 g (0.052 mol) of 2-mercapto-1-phenylethanone in 120 mL of acetonitrile was added 0.3 g (0.052 mol) of powdered potassium carbonate and 10.1 g (0.052 mol) of 3-(4-methoxyphenyl)oxiranecarboxamide. After the mixture was stirred and heated at reflux under nitrogen for 3.5 hours the solvent was removed under reduced pressure. The crude product was chromatographed on silica gel (150 g). The column was eluted with ethyl acetate, fractions 7-13 containing the product were combined and the solvent was removed under reduced pressure. The residue was crystallized from ethyl acetate to give 4.0 g (22%) of rac.-(R,*R*)-α-hydroxy-4-methoxyphenyl- β-[(2-oxo-2 -phenylethyl)thio]benzenepropanamide, mp 132°-134°.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux under nitrogen for 3.5 hours the solvent
  3. customwas removed under reduced pressure
  4. customThe crude product was chromatographed on silica gel (150 g)
  5. washThe column was eluted with ethyl acetate, fractions 7-13 containing the product
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was crystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-ca016424f88d4acdba6b9945f017e20a
Quelldatensatz
uspto-grants-1991_02
Patentnummer
US04992432

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