Ethyl cyanoacetate → Ethyl 4-acetamido-alpha-cyanocinnamate

HRID 133688

Reaktionsgleichung

Reaktionsgleichung von HRID 133688
[C:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[C:9]([NH:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1)(=[O:11])[CH3:10].N1CCCCC1>C(O)C>[C:9]([NH:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[C:3]([C:1]#[N:2])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:15][CH:14]=1)(=[O:11])[CH3:10]

Komponenten

5

Edukt 3

HCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 739424-Acetamidobenzaldehyde

Produkt 1

HCID 245851Ethyl 4-acetamido-alpha-cyanocinnamateAusbeute 41,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

A mixture of 33.9 g (0.3 mol) of ethyl cyanoacetate and 59.1 g (0.3 mol) of 4-acetamidobenzaldehyde in 300 ml of ethanol in the presence of 5 ml of piperidine is refluxed for 3 hours. The very viscous medium is diluted with 800 ml of hot ethanol. It is filtered while hot. The yellow solid obtained is washed with hot ethanol. After filtration and drying, 32 g (41% yield) of ethyl 3-(4-acetylaminophenyl)-2-cyanoacrylate are obtained in the form of a pale yellow powder.

Aufarbeitung

  1. temperatureis refluxed for 3 hours
  2. filtrationIt is filtered while hot
  3. customThe yellow solid obtained
  4. washis washed with hot ethanol
  5. filtrationAfter filtration
  6. customdrying

Quellen und Nachweise

ORD-Eintrag
ord-0de7e36560a4413c9a7044cf947d16d7
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390916B2

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