Acetyl chloride → 5-Chloroisatoic anhydride

HRID 227554

Reaktionsgleichung

Reaktionsgleichung von HRID 227554
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7](Cl)[C:3]=1[C:4]([OH:6])=[O:5].Cl[C:13](OCC)=[O:14].C([Cl:21])(=O)C>O1CCOCC1>[Cl:21][C:8]1[CH:7]=[C:3]2[C:4]([O:6][C:13](=[O:14])[NH:1][C:2]2=[CH:10][CH:9]=1)=[O:5]

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 10928Ethyl chloroformateHCID 750712-Amino-6-chlorobenzoic acid

Produkt 1

HCID 784805-Chloroisatoic anhydrideAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

2-Amino-6-chlorobenzoic acid (30 g) was suspended in 1,4-dioxane (225 ml) and ethyl chloroformate (75 ml) was added. The mixture was heated at reflux for 1 hour, then cooled to 50° C., and acetyl chloride (75 ml) was added. The mixture was stirred for 10 hours, after which the precipitated product was filtered off and washed with toluene. Drying in vacuum yields 5-chloroisatoic anhydride (33 g, 97% yield).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 hour
  3. filtrationafter which the precipitated product was filtered off
  4. washwashed with toluene
  5. customDrying in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-95d444a5725d4f3d89bff7eb6a69388c
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560557B2

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