4-(4-Chlorophenoxy)aniline → 1-[4-(4-Chloro-phenoxy)-phenyl]-pyrrolidine-2,5-dione

HRID 1972186Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1972186
[C:1]1(=[O:7])[O:6][C:4](=O)[CH2:3][CH2:2]1.[CH:8]1[C:13]([NH2:14])=[CH:12][CH:11]=[C:10]([O:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[CH:9]=1.O=S(Cl)Cl>C1(C)C=CC=CC=1>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][C:10]2[CH:11]=[CH:12][C:13]([N:14]3[C:1](=[O:7])[CH2:2][CH2:3][C:4]3=[O:6])=[CH:8][CH:9]=2)=[CH:17][CH:18]=1

Komponenten

5

Edukt 3

HCID 75784-(4-Chlorophenoxy)anilineHCID 7922Succinic anhydrideHCID 24386Thionyl Chloride

Produkt 1

HCID 218348381-[4-(4-Chloro-phenoxy)-phenyl]-pyrrolidine-2,5-dioneAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of succinic anhydride (250 mg, 2.50 mmol) and 4-amino-4′-chloro diphenylether (500 mg, 2.27 mml) in toluene is heated to 110° C. for 14 h. and cooled down to room temperature. SOCl2 (1.5 mL) is added into the mixture and stirred at room temperature for 8 h. After the solvent is removed under vacuum, the residue is treated with saturated NaHCO3 aqueous solution (20 mL) and extracted with CHCl3 (3×50 mL). The combined organic layer is washed with brine and dried (MgSO4). After filtering the drying agent, the filtrate is concentrated and purified by flash column chromatography (silica gel, EtOAc/hexane 30%˜80%) to provide 1-[4-(4-chloro-phenoxy)-phenyl]-pyrrolidine-2,5-dione as white solid (570 mg, 83%).

Aufarbeitung

  1. temperaturecooled down to room temperature
  2. customAfter the solvent is removed under vacuum
  3. additionthe residue is treated with saturated NaHCO3 aqueous solution (20 mL)
  4. extractionextracted with CHCl3 (3×50 mL)
  5. washThe combined organic layer is washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationAfter filtering the drying agent
  8. concentrationthe filtrate is concentrated
  9. custompurified by flash column chromatography (silica gel, EtOAc/hexane 30%˜80%)

Quellen und Nachweise

ORD-Eintrag
ord-27372413f40c435287ff7bf4b98e13d5
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08431607B2

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