Methyl iodide → N-[3-[3-(Dimethylamino)-1-oxo-2-propenyl]-phenyl]-N-methylacetamide

HRID 1247970Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1247970
[CH3:1][N:2]([CH3:17])[CH:3]=[CH:4][C:5]([C:7]1[CH:8]=[C:9]([NH:13][C:14](=[O:16])[CH3:15])[CH:10]=[CH:11][CH:12]=1)=[O:6].[H-].[Na+].[H][H].[CH3:22]I.[Si]([O-])([O-])([O-])[O-].[Mg+2].[Mg+2]>CN(C)C=O.C(Cl)Cl.CCCCCC>[CH3:17][N:2]([CH3:1])[CH:3]=[CH:4][C:5]([C:7]1[CH:8]=[C:9]([N:13]([CH3:22])[C:14](=[O:16])[CH3:15])[CH:10]=[CH:11][CH:12]=1)=[O:6]

Komponenten

9

Edukt 5

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66225Magnesium orthosilicateHCID 53412415N-[3-(3-Dimethylaminoacryloyl)phenyl]acetamideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 53424451N-[3-[3-(Dimethylamino)-1-oxo-2-propenyl]-phenyl]-N-methylacetamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittel2×HCID 6344DichloromethaneLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

A solution of 4.62 g of N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]acetamide in 25 ml of dimethylformamide was stirred in an inert atmosphere and 1.0 g of sodium hydride (60% oil suspension) was added. After stirring for 1 hour, the liberation of hydrogen had ceased and a solution of 3.0 g of methyl iodide in 10 ml of dimethylformamide was gradually added (with cooling, if necessary). After stirring for an additional 1 hour at room temperature, any volatiles were removed at reduced pressure and then the reaction mixture was triturated 3 times with 100 ml of hexane. The reaction mixture was carefully poured into cold water and extracted exhaustively with methylene chloride. This material was evaporated at reduced pressure to yield a yellow-orange solid. A solution of the crude solid in methylene chloride was passed through a pad of hydrous magnesium silicate. Addition of hexane to the refluxing eluate gave crystals which were collected after cooling. The desired compound was a yellow-orange crystalline material, mp 146°-148° C.

Aufarbeitung

  1. additionwas added
  2. temperature(with cooling, if necessary)
  3. stirringAfter stirring for an additional 1 hour at room temperature
  4. customany volatiles were removed at reduced pressure
  5. customthe reaction mixture was triturated 3 times with 100 ml of hexane
  6. additionThe reaction mixture was carefully poured into cold water
  7. extractionextracted exhaustively with methylene chloride
  8. customThis material was evaporated at reduced pressure
  9. customto yield a yellow-orange solid
  10. customgave crystals which
  11. customwere collected
  12. temperatureafter cooling

Quellen und Nachweise

ORD-Eintrag
ord-84ed75a9235245329e5f99eedaf91fd1
Quelldatensatz
uspto-grants-1985_06
Patentnummer
US04521422

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