Ethyl bromoacetate → Glycine, N-(4-methylphenyl)-, ethyl ester

HRID 1503642

Reaktionsgleichung

Reaktionsgleichung von HRID 1503642
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[CH2:9]([O:11][C:12](=[O:15])[CH2:13]Br)[CH3:10]>CC(C)=O>[C:5]1([CH3:8])[CH:6]=[CH:7][C:2]([NH:1][CH2:13][C:12]([O:11][CH2:9][CH3:10])=[O:15])=[CH:3][CH:4]=1

Komponenten

4

Edukt 2

HCID 7748Ethyl bromoacetateHCID 7813p-Toluidine

Produkt 1

HCID 13263396Glycine, N-(4-methylphenyl)-, ethyl esterAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

The compound was prepared according to general procedure E. To a solution of p-toluidine (4.7 mmol) in dry acetone (20 ml), ethylbromoacetate (4.7 mmol) was added. The mixture was refluxed for 3 hours. After cooling, the solvent was removed under reduced pressure. The residue was chromatogaphed on a silica gel column (dichloromethane/ethyl acetate 9/1 as eluent) to give 326 mg of ethyl 2-(p-tolylamino)acetate (yield 36%). 1H NMR (500 MHz, CDCl3): δ 1.29 (t, J=7.4 Hz, 3H), 2.28 (s, 3H), 3.90 (s, 2H), 4.26 (q, J=7.4 Hz, 2H), 6.58 (d, J=8.2 Hz, 2H), 7.05 (d, J=8.2, 2H) 13C NMR (126 MHz, CDCl3): δ 15.6, 21.8, 47.7, 62.5, 114.8, 131.2, 146.3, 172.8. MS (ESI): m/z 193.9 [M+H]+

Aufarbeitung

  1. customThe compound was prepared
  2. temperatureThe mixture was refluxed for 3 hours
  3. temperatureAfter cooling
  4. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b982dc645c2e41f0aa5aaf1091833539
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09212196B2

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