Reaktion #549924

Reaktionsgleichung

1-phthalimidopyrrole

o-chlorobenzoyl chloride

→

oil

Ausbeute 123.7%

2-(2-Chlorobenzoyl)-1-phthalimidopyrrole

Ausbeute 123.7%

Lösungsmittel

1,2-dichloroethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added freshly
2. 2
   TemperaturThe reaction mixture was heated
3. 3
   Temperaturat gentle reflux for 4.5 hours
4. 4
   Sonstigequenched with 700 ml of crushed ice and 500 ml of dichloromethane
5. 5
   SonstigeThe organic layer was separated
6. 6
   Waschenwashed with water (2×500 ml)
7. 7
   Trocknendried over anhydrous MgSO4
8. 8
   Filtrationfiltered
9. 9
   Sonstigeevaporated

Vorschrift

To a vigorously stirred mixture of 1-phthalimidopyrrole (45 g, 0.212 mol) and o-chlorobenzoyl chloride (37 g, 0.212 mole) in 500 ml of 1,2-dichloroethane was added freshly pulverized, fused zinc chloride (43.3 g, 0.318 mol) in one portion. The reaction mixture was heated at gentle reflux for 4.5 hours and then quenched with 700 ml of crushed ice and 500 ml of dichloromethane. The organic layer was separated and washed with water (2×500 ml), dried over anhydrous MgSO4, filtered, and evaporated to give 92 g of an oil. This oil was purified by column chromatography (silica gel/dichloromethane) to give 33.8 g (45%) of needles, m.p. 158°-160° C.

Quelle