ChemicalBook CAS DataBase List 1,2-Bis(maleimido)ethane

1,2-Bis(maleimido)ethane synthesis

5synthesis methods

Product Name:1,2-Bis(maleimido)ethane
CAS Number:5132-30-9
Molecular formula:C10H8N2O4
Molecular Weight:220.18

1,2-Bis(maleimido)ethane was prepared from ethylenediamine and maleic anhydride using acetic anhydride as the dehydrating agent with nickel acetate and triethylamine as catalysts. To a 1-L three-necked flask fitted with a paddle stirrer, reflux condenser, and nitrogen inlet were added 300 mL of freshly distilled N, N-dimethyl formamide, 0.5 mol (49.0 g) of maleic anhydride, and 0.25 mol (98.1 g) of ethylenediamine. The temperature of the solution rose to 115°C and its opaque color changed to yellow. Stirring was after that continued for 30 minutes at 90°C. Then 0.5 g of nickel(II) acetate, 25 mL of triethylamine, and 118 mL of acetic anhydride were added to the reaction vessel while maintaining the system at 90°C for another 30 min. The reaction mixture was cooled to 30°C, poured into 2 L of ice water, and stirred for 10 min to crystallize the BMI. The resulting brown precipitate was filtered off by suction, washed twice with 1 L of water, and filtered. For further purification, the product was dissolved in 300 mL of dry acetone, refluxed with 15 g of charcoal, and filtered. The volume of the solution was reduced to 100 mL by evaporation and then kept at 0°C overnight. The resulting precipitate was filtered off by suction and dried[1].

4,7-Epoxy-1H-isoindole-1,3(2H)-dione, 2-[2-(1,3,3a,4,7,7a-hexahydro-1,3-dioxo-4,7-epoxy-2H-isoindol-2-yl)ethyl]-3a,4,7,7a-tetrahydro-

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5132-30-9
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Yield:5132-30-9 85%

Reaction Conditions:

in 1,1,2,2-tetrachloroethane at 120; for 12 h;

Steps:

General procedure for retro-Diels-Alder reaction

General procedure: A solution of alkylated product(1 mol) in 1,1,2,2-tetrachloroethane was stirred at 120 C in an open flask for12 h. After completion of the reaction as indicated by TLC, the solvent wasevaporated under reduced pressure to afford BMI.

References:

Rao, Venkataramanarao;Navath, Suryakiran;Kottur, Mohankumar;McElhanon, James R.;McGrath, Dominic V. [Tetrahedron Letters,2013,vol. 54,# 37,p. 5011 - 5013]

55750-48-6 Synthesis