Methyl chloroacetate → methyl [3-[2-[(E)-3-(3-pyridyl)acryloylamino]ethyl]phenoxy]acetate

HRID 428135Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 428135
[OH:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[CH2:5][CH2:6][NH:7][C:8](=[O:17])/[CH:9]=[CH:10]/[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.Cl[CH2:22][C:23]([O:25][CH3:26])=[O:24].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[N:13]1[CH:14]=[CH:15][CH:16]=[C:11](/[CH:10]=[CH:9]/[C:8]([NH:7][CH2:6][CH2:5][C:4]2[CH:3]=[C:2]([CH:20]=[CH:19][CH:18]=2)[O:1][CH2:22][C:23]([O:25][CH3:26])=[O:24])=[O:17])[CH:12]=1

Komponenten

6

Edukt 4

HCID 7295Methyl chloroacetateHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 23067308(E)-N-(3-hydroxyphenethyl)-3-(3-pyridyl)-2-propenoic acid amide

Produkt 1

HCID 20701346methyl [3-[2-[(E)-3-(3-pyridyl)acryloylamino]ethyl]phenoxy]acetateAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

(E)-N-(3-hydroxyphenethyl)-3-(3-pyridyl)-2-propenoic acid amide (1.07 g, 4.0 mmol) obtained in Example 81 and methyl chloroacetate (0.52 g, 4.8 mmol) were dissolved in dimethylformamide (12 ml) and potassium carbonate (1.66 g, 12 mmol) was added and stirred at 60° C. for 8 hours. After allowing to cool, ethyl acetate was added to the reaction mixture and insoluble materials were filtered out. The filtrate was washed with water and dried over magnesium sulfate. After the solvent was distilled out under reduced pressure, the residue was recrystallized to yield the titled compound (0.83 g, 61%).

Aufarbeitung

  1. temperatureto cool
  2. filtrationwere filtered out
  3. washThe filtrate was washed with water
  4. dry with materialdried over magnesium sulfate
  5. distillationAfter the solvent was distilled out under reduced pressure
  6. customthe residue was recrystallized

Quellen und Nachweise

ORD-Eintrag
ord-5b48e717aaf54df0a5f90ef1714b17f2
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313153B1

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