Synthesis of phthalimides. An efficient and simple method enables the N-alkylation of aromatic cyclic imides using cesium carbonate as the base in anhydrous N,N-dimethylformamide at low temperatures (20-70˚C).The method is compatible with base labile functional groups.

Application

The Gabriel Synthesis Uses A “Protected” Amine (Phthalimide) In An SN2 Reaction That Does Not Undergo Over-Alkylation. ... In phthalimide, a nitrogen is flanked by two carbonyl groups. This means that the N-H is a lot more acidic than it normally would be, because the resulting anion will be resonance stabilized.