Sodium Bicarbonate → ethyl 4-[2-(N-ethoxycarbonyl-N-methylaminomethyl)morpholino]-2,3,5-trifluorobenzoate

HRID 477829Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 477829
[F:1][C:2]1[C:12]([F:13])=[C:11](F)[C:10]([F:15])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:16]([O:18][C:19]([N:21]([CH2:23][CH:24]1[O:29][CH2:28][CH2:27][NH:26][CH2:25]1)[CH3:22])=[O:20])[CH3:17].C(=O)([O-])O.[Na+]>C(#N)C>[CH2:16]([O:18][C:19]([N:21]([CH2:23][CH:24]1[CH2:25][N:26]([C:11]2[C:10]([F:15])=[CH:9][C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:2]([F:1])[C:12]=2[F:13])[CH2:27][CH2:28][O:29]1)[CH3:22])=[O:20])[CH3:17]

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 2774395Ethyl 2H-tetrafluorobenzoateHCID 146525772-(N-ethoxycarbonyl-N-methylaminomethyl)morpholine

Produkt 1

HCID 14652578ethyl 4-[2-(N-ethoxycarbonyl-N-methylaminomethyl)morpholino]-2,3,5-trifluorobenzoateAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A suspension of 22.2 g of ethyl 2,3,4,5-tetrafluorobenzoate, 22.2 g of 2-(N-ethoxycarbonyl-N-methylaminomethyl)morpholine and 8.4 g of sodium hydrogen carbonate in 130 ml of acetonitrile is refluxed for 7 hours. The reaction mixture is concentrated under reduced pressure, to the obtained residue is added 100 ml of chloroform and the solution is washed with water. After drying over anhydrous magnesium sulfate, the chloroform is distilled off under reduced pressure and the residue is puiified by chromatography on silica gel to give 29.0 g of ethyl 4-[2-(N-ethoxycarbonyl-N-methylaminomethyl)morpholino]-2,3,5-trifluorobenzoate in 72% yield, as an oily substance.

Aufarbeitung

  1. temperatureis refluxed for 7 hours
  2. concentrationThe reaction mixture is concentrated under reduced pressure, to the obtained residue
  3. additionis added 100 ml of chloroform
  4. washthe solution is washed with water
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. distillationthe chloroform is distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ecf351690b264876a0a5066aae92a573
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04889857

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