Reaktion #337648

Reaktionsgleichung

(5-amino-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid ethyl ester

benzophenone

DABCO

→

title compound

Ausbeute 52.4%

[5-(Benzhydrylidene-amino)-1,3-dioxo-1,3-dihydro-isoindol-2-yl]-acetic acid ethyl ester

Ausbeute 52.4%

Lösungsmittel

chlorobenzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeResulting mixture
2. 2
   Temperaturwas heated
3. 3
   Temperaturto reflux for 2.5 h
4. 4
   TemperaturAfter cooling
5. 5
   Sonstigereaction mixture
6. 6
   Filtrationwas filtered through a pad of celite
7. 7
   Waschenrinsed with ethyl acetate
8. 8
   EinengenFiltrate was concentrated
9. 9
   Sonstigethe residue was purified by silica gel chromatography (25%-40% ethyl acetate in hexanes)

Vorschrift

Titanium tetrachloride (1.99 g) was slowly added to a mixture of (5-amino-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid ethyl ester (3.48 g), benzophenone (2.81 g) and DABCO (4.72 g) in chlorobenzene (112 ml). Resulting mixture was heated to reflux for 2.5 h. After cooling, reaction mixture was filtered through a pad of celite and rinsed with ethyl acetate. Filtrate was concentrated and the residue was purified by silica gel chromatography (25%-40% ethyl acetate in hexanes) to give the title compound (3.03 g). MS-(+)-ion: M+1=413.3.

Quelle