Ethyl bromoacetate → HCID 15269110, Verbindung

HRID 2166341

Reaktionsgleichung

Reaktionsgleichung von HRID 2166341
[Na].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:13][NH:12][C:11](=[O:14])[CH2:10]2)=[CH:5][CH:4]=1.[CH2:15]([O:17][C:18](=[O:21])[CH2:19]Br)[CH3:16]>C(O)C>[CH2:15]([O:17][C:18](=[O:21])[CH2:19][N:12]1[CH2:13][CH:9]([C:6]2[CH:5]=[CH:4][C:3]([Cl:2])=[CH:8][CH:7]=2)[CH2:10][C:11]1=[O:14])[CH3:16]

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 1854904-(4-Chlorophenyl)-2-pyrrolidinoneHCID 5360545Sodium

Produkt 1

HCID 15269110HCID 15269110, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

13 g (565 mmol) of sodium are added in portions to 410 ml of ethanol. After it has dissolved completely, 107 g (545 mmol) of 4-(p-chlorophenyl)-2-oxopyrrolidine are added, the whole is stirred at room temperature for 2 hours, concentrated to dryness by evaporation under reduced pressure and dried overnight at 100° under reduced pressure. The resulting sodium 4-(p-chlorophenyl)-2-oxopyrrolidine is made into a slurry in 340 ml of toluene, and a solution of 63.7 ml (95.9 g; 574 mmol) of bromoacetic acid ethyl ester is added dropwise, while stirring, at 20° to 25°. The whole is stirred for a further 16 hours, concentrated to dryness by evaporation under reduced pressure at approximately 70° and partitioned between 300 ml of water and 600 ml of ethyl acetate. The organic phase is separated off, washed with saturated sodium chloride solution, dried over sodium sulphate, filtered and concentrated to dryness by evaporation under reduced pressure. 2-[4-(p-chlorophenyl)-2-oxopyrrolidin-1-yl]-acetic acid ethyl ester is obtained which, for purification, is distilled under reduced pressure; b.p.=176°-178° at 0.02 torr (0.027 mbar).

Aufarbeitung

  1. dissolutionAfter it has dissolved completely
  2. concentrationconcentrated to dryness by evaporation under reduced pressure
  3. customdried overnight at 100° under reduced pressure
  4. stirringwhile stirring, at 20° to 25°
  5. stirringThe whole is stirred for a further 16 hours
  6. concentrationconcentrated to dryness by evaporation under reduced pressure at approximately 70°
  7. custompartitioned between 300 ml of water and 600 ml of ethyl acetate
  8. customThe organic phase is separated off
  9. washwashed with saturated sodium chloride solution
  10. dry with materialdried over sodium sulphate
  11. filtrationfiltered
  12. concentrationconcentrated to dryness by evaporation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-adddd17015a244b4afd7eaf2d6ad110c
Quelldatensatz
uspto-grants-1990_07
Patentnummer
US04945092

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