Hydrochloric Acid → cinnamyl-N-methyl-3,4,5-trimethoxyphenylpropiolamide

HRID 1282921Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1282921
[CH3:1][NH:2][C:3](=[O:18])[C:4]#[C:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH3:15])=[C:8]([O:16][CH3:17])[CH:7]=1.[H-].[Na+].[CH2:21](Br)[CH:22]=[CH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl>CN(C)C=O.O>[CH2:21]([N:2]([CH3:1])[C:3](=[O:18])[C:4]#[C:5][C:6]1[CH:7]=[C:8]([O:16][CH3:17])[C:9]([O:14][CH3:15])=[C:10]([O:12][CH3:13])[CH:11]=1)[CH:22]=[CH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 98116BromomethylstyreneHCID 21445696N-methyl-3,4,5-trimethoxyphenylpropiolamide

Produkt 1

HCID 54089509cinnamyl-N-methyl-3,4,5-trimethoxyphenylpropiolamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

The solution of 10.0 g of N-methyl-3,4,5-trimethoxyphenylpropiolamide in 80 ml of dimethylformamide is added dropwise to the suspension of 1.05 g of sodium hydride in 10 ml of dimethylformamide while stirring and cooling with ice. The mixture is stirred for 1 hour at room temperature whereupon the solution of 8.0 g of cinnamyl bromide in 40 ml of dimethylformamide is added dropwise and stirring is continued for 15 hours at room temperature. The mixture is poured into the solution of 20 ml of 3N hydrochloric acid in 600 ml of water and the whole is extracted with 250 ml of toluene. The extract is washed with 2N aqueous sodium hydroxide and saturated aqueous sodium chloride, dried and filtered, to yield the desired toluene-solution of the N-cinnamyl-N-methyl-3,4,5-trimethoxyphenylpropiolamide.

Aufarbeitung

  1. temperaturecooling with ice
  2. additionis added dropwise
  3. stirringstirring
  4. extractionthe whole is extracted with 250 ml of toluene
  5. washThe extract is washed with 2N aqueous sodium hydroxide and saturated aqueous sodium chloride
  6. customdried
  7. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-14bb0fa91c264522942f62d1377cb02c
Quelldatensatz
uspto-grants-1976_08
Patentnummer
US03973030

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