Phenylacetonitrile → 3-(Dimethylamino)-2-phenylacrylonitrile

HRID 1779392Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1779392
[CH2:1]([C:8]#[N:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[CH:12](OC)[N:13]([CH3:15])[CH3:14]>CO>[C:8]([C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[CH:12][N:13]([CH3:15])[CH3:14])#[N:9]

Komponenten

4

Edukt 2

HCID 8794PhenylacetonitrileHCID 78373Dimethylformamide dimethyl acetal

Produkt 1

HCID 37978433-(Dimethylamino)-2-phenylacrylonitrileAusbeute 77,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A stirred solution of 5.1 grams (0.044 mole) of benzyl cyanide and 8.7 grams (0.065 mole) of N,N-dimethylformamide dimethyl acetal in 150 mL of methanol was heated at reflux for about 20 hours. After this time gas chromatographic analysis of the reaction mixture indicated that the reaction was not complete. An additional 3.0 mL of the intermediate acetal (total--0.088 mole) was added, and the heating at reflux was continued an additional 24 hours. After this time the reaction mixture was concentrated under reduced pressure to a residue. The residue was triturated with 25% methylene chloride in petroleum ether, yielding 5.9 grams of 1-cyano-1-phenyl-2-(N,N-dimethylamino)ethene. The NMR spectrum was consistent with the proposed structure.

Aufarbeitung

  1. temperatureat reflux for about 20 hours
  2. temperaturethe heating at reflux
  3. concentrationAfter this time the reaction mixture was concentrated under reduced pressure to a residue
  4. customThe residue was triturated with 25% methylene chloride in petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-55118f01321b463e81cf398454f5672b
Quelldatensatz
uspto-grants-1997_05
Patentnummer
US05627189

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