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Oxalyl chloride → 4-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoyl chloride

HRID 1614696
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1614696
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14](=[O:15])[CH:13]=[CH:12][C:11]2=[O:16])=[CH:6][CH:5]=1)(O)=[O:2].C(Cl)(=O)C([Cl:20])=O>C1C=CC=CC=1>[C:14]1(=[O:15])[N:10]([C:7]2[CH:8]=[CH:9][C:4]([C:1]([Cl:20])=[O:2])=[CH:5][CH:6]=2)[C:11](=[O:16])[CH:12]=[CH:13]1
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Komponenten

4

Edukt 2

HCID 65578Oxalyl chlorideHCID 869254-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)benzoic acid

Produkt 1

HCID 133654044-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

Para-maleimidobenzoyl chloride was prepared in accordance with the procedure described by Adams et al. in J. Am. Chem. Soc , 42, 599 (1920). The N-(para-carboxyphenyl) maleimide (15 g) was suspended in about 80 ml of benzene with stirring. To this mixture was added 15 ml (a 2.5:1 molar excess) of oxalyl chloride, whereupon some gas was evolved. The mixture was then heated slowly to reflux and maintained at reflux for two hours. Excess oxalyl chloride was removed by distillation. The reaction mixture was then cooled and the yellow product recovered by suction filtration. The resultant product was washed with hexane and dried under vacuum at room temperature.

Aufarbeitung

  1. additionTo this mixture was added 15 ml (a 2.5
  2. temperatureThe mixture was then heated slowly
  3. temperatureto reflux
  4. temperaturemaintained
  5. temperatureat reflux for two hours
  6. customExcess oxalyl chloride was removed by distillation
  7. temperatureThe reaction mixture was then cooled
  8. filtrationthe yellow product recovered by suction filtration
  9. washThe resultant product was washed with hexane
  10. customdried under vacuum at room temperature

Quellen und Nachweise

ORD-Eintrag
ord-18d86bbc782e4c05af8269f2446f5e8a
Quelldatensatz
uspto-grants-1993_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05198551

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