ethyl 2-bromo-3-oxo-3-phenylpropanoate → HCID 44384908, Verbindung

HRID 1530006Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1530006
[N:1]1[CH:6]=[CH:5][C:4]([C:7](=[S:9])[NH2:8])=[CH:3][CH:2]=1.Br[CH:11]([C:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13]>C(O)C>[C:18]1([C:17]2[N:8]=[C:7]([C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)[S:9][C:11]=2[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

4

Edukt 2

HCID 237819ethyl 2-bromo-3-oxo-3-phenylpropanoateHCID 27237884-Pyridinecarbothioamide

Produkt 1

HCID 44384908HCID 44384908, VerbindungAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a suspension of pyridine-4-carbothioamide (2.9 g, 21 mmol) in ethanol (150 mL) was added ethyl 2-bromo-3-oxo-3-phenylpropanoate (5.9 g, 22 mmol), and the mixture was heated under reflux for 8 hr. The reaction solution was allowed to cool to room temperature, and the solid was collected by filtration, washed with diethyl ether, dried, suspended in ethyl acetate (250 mL), and washed with saturated aqueous sodium bicarbonate solution (150 mL×2). The combined aqueous layer was extracted with ethyl acetate (100 mL×2). The combined organic layer was dried over anhydrous magnesium sulfate, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was washed with diethyl ether, and collected by filtration to give the title compound (3.7 g, 57%) as a colorless solid.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 8 hr
  3. filtrationthe solid was collected by filtration
  4. washwashed with diethyl ether
  5. customdried
  6. washwashed with saturated aqueous sodium bicarbonate solution (150 mL×2)
  7. extractionThe combined aqueous layer was extracted with ethyl acetate (100 mL×2)
  8. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  9. filtrationthe insoluble material was filtered off
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. washThe residue was washed with diethyl ether
  12. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-60ff47c929ca4ef1908c1cdce0bb0e14
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090601B2

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