Aniline → N-Phenylglycine ethyl ester

HRID 342724

Reaktionsgleichung

Reaktionsgleichung von HRID 342724
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].C([O-])(=O)C.[Na+]>C(O)C>[C:2]1([NH:1][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 6115AnilineHCID 7748Ethyl bromoacetateHCID 517045Sodium Acetate

Produkt 1

HCID 75190N-Phenylglycine ethyl esterAusbeute 3,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of aniline (9.7 g, 104 mmol) and ethyl bromoacetate (16.3 g, 98 mmol) in 150 mL of absolute ethanol was added solid sodium acetate (8.1 g, 99 mmol) in portions. After stirring at room temperature, the solvent was removed by rotary evaporator and the residue suspended in diethyl ether, filtered through Celite and concentrated. Chromatography of the crude residue on silica gel using 20-80 ethyl acetate-hexane as eluant gave the title compound (580 mg) as a light brown solid. The structure was supported by NMR, infrared spectroscopy, elemental analysis, and mass spectroscopy.

Aufarbeitung

  1. customthe solvent was removed by rotary evaporator
  2. filtrationfiltered through Celite
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-49dc83e551c24b57976fb876184fc779
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05859052

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