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Water → 2,4-Dichloro-5-(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl) benzaldehyde (O-methyl)oxime

HRID 566610
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 566610
[CH3:1][O:2][N:3]=[CH:4][C:5]1[CH:10]=[C:9]([NH2:11])[C:8]([Cl:12])=[CH:7][C:6]=1[Cl:13].[C:14]1(=O)[O:19][C:17](=[O:18])[C:16]2[CH2:20][CH2:21][CH2:22][CH2:23][C:15]1=2.O>C(O)(=O)C>[CH3:1][O:2][N:3]=[CH:4][C:5]1[CH:10]=[C:9]([N:11]2[C:17](=[O:18])[C:16]3[CH2:20][CH2:21][CH2:22][CH2:23][C:15]=3[C:14]2=[O:19])[C:8]([Cl:12])=[CH:7][C:6]=1[Cl:13]
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Komponenten

5

Edukt 3

HCID 962WaterHCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 572209565-amino-2,4-dichlorobenzaldehyde (O-methyl)oxime

Produkt 1

HCID 570118122,4-Dichloro-5-(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl) benzaldehyde (O-methyl)oxime

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

18 g (82 mmol) of 5-amino-2,4-dichlorobenzaldehyde (O-methyl)oxime were added to a solution of 12.5 g (82 mmol) of 3,4,5,6-tetrahydrophthalic anhydride in 300 ml of acetic acid, whereupon the mixture was stirred for 15 hours at reflux temperature. The reaction mixture was subsequently poured into 1 l water. The product was then extracted with 300 ml of methyl tert-butyl ether. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, dried over magnesium sulfate and finally concentrated. The residue was purified by means of silica gel chromatography (eluent: hexane/ethyl acetate=4:1). Yield: 20.9 g; m.p.: 122-124° C.

Aufarbeitung

  1. temperatureat reflux temperature
  2. extractionThe product was then extracted with 300 ml of methyl tert-butyl ether
  3. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationfinally concentrated
  6. customThe residue was purified by means of silica gel chromatography (eluent: hexane/ethyl acetate=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-9057637936d2479ab82734c54c531b70
Quelldatensatz
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06175007B1

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