Water → 3-(2-(4-Chlorophenoxy)phenyl)-1-methylpyrrolidine-2,4-dione

HRID 2040931Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2040931
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH2:13][C:14]([N:16]([CH3:22])[CH2:17][C:18](OC)=[O:19])=[O:15])=[CH:4][CH:3]=1.[Na].O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH:13]2[C:18](=[O:19])[CH2:17][N:16]([CH3:22])[C:14]2=[O:15])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 5360545SodiumHCID 58729181Methyl N-(2-(2-(4-chlorophenoxy)phenyl)acetyl)-N-methylglycinate

Produkt 1

HCID 231486583-(2-(4-Chlorophenoxy)phenyl)-1-methylpyrrolidine-2,4-dioneAusbeute 21,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

27.8 g (79.9 mmol) of methyl N-{2-[2-(4-chlorophenoxy)phenyl]-1-oxoethyl}-N-methylglycinate (compound IIIb) was dissolved in 150 mL of toluene. 11.5 g of sodium tert-butoxyde were added, and the resulting mixture was stirred overnight at room temperature. 350 mL of water were added, and the resulting mixture was extracted three times with 150 mL of ethyl acetate. The combined organic phases were washed with 200 mL of water. The aqueous phases were combined and pH was adjusted to 1 with HCl 2 M. The solvent was removed by filtration, and the solid was recrystallized twice with methanol, to obtain 5.4 g of 3-[2-(4-chlorophenoxy)phenyl]-1-methylpyrrolidine-2,4-dione (compound IVb) as a solid. Yield: 21.4%.

Aufarbeitung

  1. extractionthe resulting mixture was extracted three times with 150 mL of ethyl acetate
  2. washThe combined organic phases were washed with 200 mL of water
  3. customThe solvent was removed by filtration
  4. customthe solid was recrystallized twice with methanol

Quellen und Nachweise

ORD-Eintrag
ord-68de4a0256ee4bd991a57ed106107a5c
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08580972B2

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