Reaktion #467901

ord-94448e8b87084c39ae84e619c07fa7d8

Reaktionsgleichung

Cl
hydrogen chloride
O=C(O)c1cc([N+](=O)[O-])cc([N+](=O)[O-])c1
3,5 dinitrobenzoic acid
O=S(Cl)Cl
thionyl chloride
O=C(O)c1cccc([N+](=O)[O-])c1[N+](=O)[O-]
dinitrobenzoic acid
→
O=C(Cl)c1cc([N+](=O)[O-])cc([N+](=O)[O-])c1
3,5-dinitrobenzoic chloride
Ausbeute 90.0%

Edukte

Cl
hydrogen chloride
O=C(O)c1cc([N+](=O)[O-])cc([N+](=O)[O-])c1
3,5 dinitrobenzoic acid
O=S(Cl)Cl
thionyl chloride
O=C(O)c1cccc([N+](=O)[O-])c1[N+](=O)[O-]
dinitrobenzoic acid

Reagenzien

Keine

Lösungsmittel

CCOC(C)=O
ethyl acetate
CN(C)C=O
DMF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigethe reaction mixtures
  2. 2
    Temperaturwere refluxed
  3. 3
    EinengenThe reacted solution was concentrated until a solid
  4. 4
    Sonstigecould be precipitated
  5. 5
    workup.ADDITIONwas poured into hexane
  6. 6
    Sonstigethe precipitated solid was separated by filtration

Vorschrift

3,5 dinitrobenzoic acid and ethyl acetate were placed in a reaction vessel. While thionyl chloride with some drops of DMF (about double as many moles as dinitrobenzoic acid) was dropped into the reaction mixtures, the reaction mixtures were refluxed with stirring until the generation of hydrogen chloride gas stopped. The reacted solution was concentrated until a solid could be precipitated and was poured into hexane and then the precipitated solid was separated by filtration. 3,5-dinitrobenzoic chloride was obtained in a 90% yield.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06303742B1uspto-grants-2001_10