Uses
N-Benzylmaleimide is used as plastic additive, Pharmaceutical Intermediates. It is an important raw material intermediate used in organic Synthesis, Pharmaceuticals, Agrochemicals Dyestuff.
Synthesis
GENERAL PROCEDURE: At room temperature, benzylamine (17 mmol) was slowly added dropwise to a solution of maleic anhydride (20 mmol) dissolved in acetic acid (10 mL) to form a suspension. Subsequently, the reaction mixture was stirred under reflux conditions overnight. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was dissolved in chloroform (100 mL) and extracted by partition with deionized water (30 mL). The aqueous phase was further extracted with chloroform (3 x 50 mL). All organic phases were combined and washed sequentially with saturated aqueous sodium bicarbonate (30 mL) and brine (30 mL). The organic phases were dried over anhydrous sodium sulfate, filtered and concentrated. Finally, the concentrated residue was purified by silica gel column chromatography to obtain N-benzylmaleimide.
References
[1] Journal of Chemical Research - Part S, 1998, # 5, p. 272 - 273
[2] Journal of the Chinese Chemical Society, 2009, vol. 56, # 4, p. 839 - 842
[3] Synthesis, 2004, # 7, p. 995 - 998
[4] Tetrahedron Letters, 1997, vol. 38, # 46, p. 8089 - 8092
[5] Tetrahedron Asymmetry, 2008, vol. 19, # 18, p. 2115 - 2118
