Reaktion #2352

Reaktionsgleichung

m-phenylenediamine

citraconic anhydride

→

N,N'-(m-phenylene)bis citraconamic acid

Ausbeute 99.9%

Lösungsmittel

acetone

—

reagent

acetone

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeflushed with nitrogen
2. 2
   SonstigeThe flask was fitted with a reflux condenser, mechanical stirrer
3. 3
   workup.ADDITIONthe solution added dropwise over about 1 1/2 hours
4. 4
   TemperaturThe reaction mixture was refluxed for an additional hour
5. 5
   Filtrationsuction filtered

Vorschrift

A 3-liter, 3-neck round bottom flask was charged with 54 g (0.5 mole) of m-phenylenediamine and 500 ml of reagent acetone and flushed with nitrogen. The flask was fitted with a reflux condenser, mechanical stirrer and thermocouple. A dropping funnel containing 112 g (1.0 mole) of citraconic anhydride in 500 ml of reagent acetone was attached and the solution added dropwise over about 1 1/2 hours with stirring as the temperature was allowed to rise to reflux the acetone. The reaction mixture was refluxed for an additional hour, cooled to room temperature and suction filtered to give 166 g of N,N'-(m-phenylene)bis citraconamic acid as shown by NMR analysis, as a tan mustard-colored solid melting at 152°-156° C.

Quelle