Potassium Carbonate → Ethyl 4-(6-acetyl-3-(N,N-dimethylcarbamoylthio)-2-propylphenoxy)butyrate

HRID 488691Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 488691
[CH3:1][N:2]([CH3:19])[C:3]([S:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:14])[CH3:13])=[C:8]([OH:15])[C:7]=1[CH2:16][CH2:17][CH3:18])=[O:4].Br[CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.[I-].[K+]>[C:12]([C:9]1[C:8]([O:15][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:7]([CH2:16][CH2:17][CH3:18])[C:6]([S:5][C:3](=[O:4])[N:2]([CH3:1])[CH3:19])=[CH:11][CH:10]=1)(=[O:14])[CH3:13]

Komponenten

6

Edukt 3

HCID 11430Potassium Carbonate2×HCID 76300Ethyl 4-bromobutyrateHCID 2801555S-(4-Acetyl-3-hydroxy-2-propylphenyl) dimethylcarbamothioate

Produkt 1

HCID 15712394Ethyl 4-(6-acetyl-3-(N,N-dimethylcarbamoylthio)-2-propylphenoxy)butyrateAusbeute 84,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 4875Potassium IodideKatalysatorHCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of (4-(N,N-dimethylcarbamoylthio)-2-hydroxy-3-propylphenyl)ethanone (26.6 g), ethyl 4-bromobutyrate (92.9 g), potassium iodide (1 g) and potassium carbonate (26.1 g) in acetone (200 ml) was heated and refluxed with stirring. Each of potassium carbonate (13 g) was added thereto after 9 hours and 14 hours, and the mixture was heated and refluxed with stirring for total 29 hours. Then, inorganic materials were separated and the solution was concentrated under a reduced pressure. The resultant residue was purified through silica-gel column chromatography (eluting with hexane, then benzene and finally benzene:ethyl acetate=9:1) to give ethyl 4-(6-acetyl-3-(N,N-dimethylcarbamoylthio) -2-propylphenoxy)butyrate (31.5 g, 84.2%) as light brown crystal, mp 60-63° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperaturerefluxed
  3. temperature14 hours, and the mixture was heated
  4. temperaturerefluxed
  5. stirringwith stirring for total 29 hours
  6. customThen, inorganic materials were separated
  7. concentrationthe solution was concentrated under a reduced pressure
  8. customThe resultant residue was purified through silica-gel column chromatography (
  9. washeluting with hexane

Quellen und Nachweise

ORD-Eintrag
ord-b93701a9aa444ecab00fdb80d279d0ff
Quelldatensatz
uspto-grants-2005_12
Patentnummer
USRE038921E1

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