Dimethylformamide → 2-(N-Ethyl-4-formylanilino)ethyl benzoate

HRID 249050Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 249050
P(Cl)(Cl)(Cl)=O.[CH2:6]([N:8]([CH2:15][CH2:16][O:17][C:18](=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:7].[OH-].[Na+].CN(C)[CH:30]=[O:31]>>[CH:30]([C:12]1[CH:13]=[CH:14][C:9]([N:8]([CH2:6][CH3:7])[CH2:15][CH2:16][O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:10][CH:11]=1)=[O:31]

Komponenten

5

Edukt 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 1040102-(Ethylanilino)ethyl benzoate

Produkt 1

HCID 1045642-(N-Ethyl-4-formylanilino)ethyl benzoateAusbeute 82 %

Versuchsvorschrift

Phosphorous oxychloride (0.33mL, 3.5 mmol) was added to dry dimethylformamide (3 mL) at 0° C. for 15 minutes. After cooling to room temperature, N-ethyl-(2-benzoyloxyethyl)aniline (1 g, 3.5 mmol) was added followed by stirring at room temperature for 5 minutes and then at 90° C. for 30 minutes. The dark green solution was then cooled to room temperature and made basic to pH 8 by addition of 1 molar sodium hydroxide solution. Product was extracted into diethyl ether (3×20 mL). The combined ether extracts were washed with water (30 mL), saturated sodium chloride (30 mL), dried over magnesium sulfate and solvent removed under reduced pressure. Product was isolated as a clear yellow oil (0.90 g, 82% yield).

Aufarbeitung

  1. waitat 90° C. for 30 minutes
  2. temperatureThe dark green solution was then cooled to room temperature
  3. extractionProduct was extracted into diethyl ether (3×20 mL)
  4. washThe combined ether extracts were washed with water (30 mL), saturated sodium chloride (30 mL)
  5. dry with materialdried over magnesium sulfate and solvent
  6. customremoved under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ac51e15b892a4d67bda63218f27c8f82
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05212269

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