Acetic Acid → 2-Cyano-5-(dimethylamino)-N,N-dimethylpenta-2,4-dienamide

HRID 1591277

Reaktionsgleichung

Reaktionsgleichung von HRID 1591277
[CH3:1][N:2]([CH3:7])[CH:3]=[CH:4][CH:5]=O.[CH3:8][N:9]([CH3:15])[C:10](=[O:14])[CH2:11][C:12]#[N:13].N1CCCCC1.C(O)(=O)C>C1(C)C=CC=CC=1.O>[C:12]([C:11]([C:10]([N:9]([CH3:15])[CH3:8])=[O:14])=[CH:5][CH:4]=[CH:3][N:2]([CH3:7])[CH3:1])#[N:13]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 791253-(Dimethylamino)-2-propenalHCID 2511432-Cyano-N,N-dimethylacetamide

Produkt 1

HCID 545707072-Cyano-5-(dimethylamino)-N,N-dimethylpenta-2,4-dienamideAusbeute 70,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 1140TolueneLösungsmittel

Versuchsvorschrift

3-Dimethylaminoacrolein (25 g, 0.25 mol) and cyanoacetic acid N,N-dimethylamide (28 g, 0.25 mol) were dissolved in toluene (250 ml) and piperidine (1 ml) and acetic acid (2.5 ml) were then added. The solution was heated under reflux in a water separator until no more water was formed (about 2 hours). The solution was then filtered and reduced to about 100 ml. On cooling, crystals formed which were filtered off under suction and dried to give 34 g 1-cyano-1- dimethylaminocarbonyl-4-dimethylamino-1,3-butadiene as yellow-brown crystals, m.pt. 149°-150° C.

Aufarbeitung

  1. temperatureThe solution was heated
  2. customwas formed (about 2 hours)
  3. filtrationThe solution was then filtered
  4. temperatureOn cooling
  5. customcrystals formed which
  6. filtrationwere filtered off under suction
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-2d74e6310d284c6db3fc4c34764ee7ea
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05206372

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