Sodium Bicarbonate → (E)-N-[2-(3,4-dimethoxyphenyl)-2-(methylthio)ethyl]-3-(3-pyridyl)-2-propenamide

HRID 428147

Reaktionsgleichung

Reaktionsgleichung von HRID 428147
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([S:14][CH3:15])[CH2:12][NH2:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[N:16]1[CH:21]=[CH:20][CH:19]=[C:18](/[CH:22]=[CH:23]/[C:24](O)=[O:25])[CH:17]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([S:14][CH3:15])[CH2:12][NH:13][C:24](=[O:25])/[CH:23]=[CH:22]/[C:18]2[CH:17]=[N:16][CH:21]=[CH:20][CH:19]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Komponenten

6

Edukt 3

HCID 516892Sodium BicarbonateHCID 776396trans-3-(3-Pyridyl)acrylic acidHCID 14446612HCID 14446612, Verbindung

Produkt 1

HCID 20701371(E)-N-[2-(3,4-dimethoxyphenyl)-2-(methylthio)ethyl]-3-(3-pyridyl)-2-propenamideAusbeute 52,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of the crude oily 2-(3,4-dimethoxy-phenyl) -2-(methylthio)ethylamine (0.96 g) and trans-3-(3-pyridyl) acrylic acid (0.63 g, 4.2 mmol) in dimethylformamide (10 ml), diethylphosphoric cyanide (0.69 ml) and triethylamine (1.17 ml) were sequentially added under ice-cooling and stirred for 10 minutes under ice-cooling. Aqueous sodium bicarbonate solution was added to the reaction mixture and extracted with ethyl acetate. The organic layers were combined, washed with water and aqueous saturated sodium chloride solution and dried over magnesium sulfate. The solvent was distilled out under reduced pressure and the residue was purified by silica gel column chromatography (hexane: chloroform:ethanol=8:2:1) to yield the titled compound (788 mg, 47%).

Aufarbeitung

  1. temperaturecooling
  2. temperaturecooling
  3. extractionextracted with ethyl acetate
  4. washwashed with water and aqueous saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled out under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (hexane: chloroform:ethanol=8:2:1)

Quellen und Nachweise

ORD-Eintrag
ord-882e318f99a64b5b911b33cb022ceb3c
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313153B1

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