Potassium phthalimide

Chemical properties

slight yellow-green to white powder

The Uses of Potassium phthalimide

Condensation of phthalimide potassium with organic halide in dimethylformamide has been reported. Reaction of potassium phthalimide and sulfur monochloride in petroleum ether has been studied.

Description

Potassium phthalimide is a versatile intermediate in organic synthesis with a range of applications. It is utilized in the synthesis of N-alkylated phthalimides, which are key in the preparation of primary amines through the Gabriel synthesis method and subsequent hydrolysis reaction. Beyond its role in amine synthesis, potassium phthalimide is also an essential intermediate in the production of synthetic indigo, pigments, dyes, and pharmaceuticals. Furthermore, it functions as an organocatalyst, facilitating the cyanosilylation of various carbonyl compounds under mild conditions. Additionally, it is employed as a reagent for converting allyl- and alkyl halides into protected primary amines, highlighting its importance in the synthesis of a variety of chemical compounds.

What are the applications of Application

Potassium phthalimide is used as an intermediate in the synthesis of N-alkylated phthalimides, which is involved in the preparation of primary amines (Gabriel synthesis) by the hydrolysis reaction. It is also used as an intermediate for synthetic indigo, pigments, dyes and pharmaceuticals. Further, it is employed as an organocatalyst for the cyanosilylation of various carbonyl compounds under extremely mild conditions. In addition to this, it serves as a reagent for the transformation of allyl- and alkyl halides into protected primary amines.

Purification Methods

The solid may contain phthalimide and K2CO3 from hydrolysis. If too much hydrolysis has occurred (this can be checked by extraction with cold Me2CO in which the salt is insoluble, evaporate the Me2CO and weigh the residue), it would be better to prepare it afresh. If little hydrolysis has occurred, then recrystallise it from a large volume of EtOH, and wash the solid with a little Me2CO and dry it in a continuous vacuum to constant weight. [Salzerg & Supriawski Org Synth Coll Vol I 119 1941, Raman & IR: Hase J Mol Struct 48 33 1978, Dykman Chem Ind (London) 40 1972, IR, NMR: Assef et al. Bull Soc Chim Fr II 167 1979, Beilstein 21/10 V 270.]