Dichloromaleic anhydride → 3,4-Dichloro-1-[2-(difluoromethoxy)phenyl]-1H-pyrrole-2,5-dione

HRID 1263051

Reaktionsgleichung

Reaktionsgleichung von HRID 1263051
[Cl:1][C:2]1[C:3]([O:5][C:6](=[O:9])[C:7]=1[Cl:8])=O.[F:10][CH:11]([F:20])[O:12][C:13]1[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=1[NH2:15]>O1CCOCC1>[Cl:8][C:7]1[C:6]([N:15]([C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[O:12][CH:11]([F:10])[F:20])[C:3](=[O:5])[C:2]=1[Cl:1])=[O:9]

Komponenten

4

Edukt 2

HCID 70728Dichloromaleic anhydrideHCID 9346202-(Difluoromethoxy)aniline

Produkt 1

HCID 130730543,4-Dichloro-1-[2-(difluoromethoxy)phenyl]-1H-pyrrole-2,5-dioneAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

16.7 g (0.1 mole) of 2,3-dichloromaleic anhydride is dissolved in 100 ml of dioxane, and a solution of 15.9 g (0.1 mole) of o-difluoromethoxyaniline in 30 ml of dioxane is added dropwise to it at room temperature over 20 minutes with stirring. Thereafter, the resulting solution is stirred at 70°-80° C. for 2 hours and the dioxane is then distilled off under a reduced pressure. Water is added to the residue to precipitate crystals. The precipitated crystals are filtered off and recrystallized from ethanol to give 27.7 g (yield: 90%) of 2,3-dichloro-N-(o-difluoromethoxyphenyl)maleimide melting at 103.5°-104° C. in the form of light yellow crystals.

Aufarbeitung

  1. stirringThereafter, the resulting solution is stirred at 70°-80° C. for 2 hours
  2. distillationthe dioxane is then distilled off under a reduced pressure
  3. additionWater is added to the residue
  4. customto precipitate crystals
  5. filtrationThe precipitated crystals are filtered off
  6. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-6ed2696af47c4999a62c91662e42309f
Quelldatensatz
uspto-grants-1984_06
Patentnummer
US04455315

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