Acetone → N-(2-methyl-4,5-dimethoxyphenyl)cinnamamide

HRID 1900871Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1900871
[CH3:1][O:2][C:3]1[C:9]([O:10][CH3:11])=[CH:8][C:6]([NH2:7])=[C:5]([CH3:12])[CH:4]=1.N1C=CC=CC=1.CC(C)=O.[C:23](Cl)(=[O:32])[CH:24]=[CH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O>[CH3:12][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:9]([O:10][CH3:11])=[CH:8][C:6]=1[NH:7][C:23](=[O:32])[CH:24]=[CH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Komponenten

6

Edukt 4

HCID 180AcetoneHCID 1049PyridineHCID 660233-Phenylprop-2-enoyl chlorideHCID 2665854,5-Dimethoxy-2-methylaniline

Produkt 1

HCID 53987657N-(2-methyl-4,5-dimethoxyphenyl)cinnamamideAusbeute 97,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 4,5-dimethoxy-2-methylaniline (40.1 g), pyridine (48.5 ml), and acetone (350 ml), cinnamoyl chloride (44.0 g) was added dropwise at room temperature over 15 minutes. After allowing to react at room temperature for 2 hours, water (15 ml) was added and the mixture was stirred for 20 minutes. The solvent was distilled off under reduced pressure, and the residue was dissolved in chloroform, followed by washing with 1N HCl, 1N caustic soda and water in this order, and drying. Chloroform was evaporated. Precipitated crystals were collected by filtration with ether. 69.8 g of the title compound was obtained as yellow crystals (97.8%).

Aufarbeitung

  1. customto react at room temperature for 2 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform
  4. washby washing with 1N HCl, 1N caustic soda and water in this order
  5. customdrying
  6. customChloroform was evaporated
  7. customPrecipitated crystals
  8. filtrationwere collected by filtration with ether

Quellen und Nachweise

ORD-Eintrag
ord-fb28d69fdfc242a5bcd10c8088961451
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05576324

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