Thionyl Chloride → 3-Chloroisatoic anhydride

HRID 838992

Reaktionsgleichung

Reaktionsgleichung von HRID 838992
C([O:3][C:4]([NH:6][C:7]1[C:8](=[CH:12][CH:13]=[CH:14][C:15]=1[Cl:16])[C:9]([OH:11])=[O:10])=O)C.S(Cl)(Cl)=O>O1CCOCC1>[Cl:16][C:15]1[C:7]2[NH:6][C:4](=[O:3])[O:10][C:9](=[O:11])[C:8]=2[CH:12]=[CH:13][CH:14]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 203255893-Chloro-2-[(ethoxycarbonyl)amino]benzoic acid

Produkt 1

HCID 5175353-Chloroisatoic anhydride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

468 gm of N-ethoxycarbonyl-3-chloro-anthranilic acid (m.p. 111°-114° C) were refluxed in 1500 ml of dioxane with 420 ml of thionyl chloride for 3 hours while stirring. Thereafter, the reaction solution was evaporated in vacuo until crystallization started, and then cooled. The precipitate was collected by suction filtration and washed with ether. 8-Chloro-2H-3,1-benzoxazine-2,4(1H)-dione, m.p. 225°-230° C, was obtained.

Aufarbeitung

  1. customThereafter, the reaction solution was evaporated in vacuo until crystallization
  2. temperaturecooled
  3. filtrationThe precipitate was collected by suction filtration
  4. washwashed with ether

Quellen und Nachweise

ORD-Eintrag
ord-eabb9a499dfa4e3fa44b3f4e83befdd6
Quelldatensatz
uspto-grants-1978_06
Patentnummer
US04093734

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