Chemical Properties
light yellow crystals
Uses
N-Methylmaleimide is an electron deficient olefin that acts as a thiol-blocking reagent.
Synthesis Reference(s)
The Journal of Organic Chemistry, 60, p. 6676, 1995
DOI: 10.1021/jo00126a013
Synthesis
GENERAL METHOD: Methylamine hydrochloride (19.1 g, 0.30 mol) was added to a solution of acetic acid (40 mL) containing maleic anhydride (20 g, 0.20 mol) and potassium acetate (30.0 g, 0.30 mol) and stirred thoroughly. The mixture was heated to reflux temperature (110 °C) and the reaction was maintained for 4 hours. Upon completion of the reaction, the reaction mixture was cooled to 25-30 °C. Subsequently, the reaction mixture was slowly poured into pre-cooled sodium bicarbonate solution (100 mL) and extracted with diethyl ether (3 x 70 mL). The organic layers were combined, washed with brine solution and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure to give N-methylmaleimide (6.89 g, 30% yield).
Purification Methods
Crystallise the imide three times from diethyl ether. Dry it in vacuo.[Beilstein 21/10 V 5.]
References
[1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 15, p. 4577 - 4580
