N,N'-(4-METHYL-1,3-PHENYLENE)BISMALEIMIDE synthesis

Yield:-

Reaction Conditions:

with 1-methyl-pyrrolidin-2-one;hydroquinone in toluene;

Steps:

1 Synthesis of 2,4-bis(maleimido)toluene

Example 1 Synthesis of 2,4-bis(maleimido)toluene A mixture of 523 g toluene, 15 g N-methylpyrrolidone, 0.3 g hydroquinone and 98.1 g/1.0 mole maleic anhydride is heated to 60° C., while stirring, and 62 g/0.5 mole 2,4-toluylenediamine are metered in over a period of 3 hours. The mixture is subsequently stirred for 3 hours, 7.0 g para-toluenesulfonic acid are added and the contents of the flask are brought to the boiling point at 110° C., while stirring. After 8.25 hours, the azeotropic separation of water has ended and the solution is poured through a folded filter and left to cool to crystallize out. The precipitate is filtered off with suction, dried at 70° C. in vacuo and comminuted. Yield: 100 g (corresponds to 71% of theory). The substance was characterized by elemental analysis, TLC, IR and the melting point. Melting point: 160-164° C. Elemental analysis: C₁₅ H₁₀ N₂ O₄ (282.3 g/mole) calc.: C: 63.8 H: 3.6 N: 9.9 found: C: 64.2 H: 3.9 N: 9.9 TLC (mobile phase: ethanol, support material: silica gel): R_f value:0.69 IR: 1700 cm^-1 stretching vibrations C=O 3100 cm^-1 stretching vibrations C_(arom.) --H 3500 cm^-1 stretching vibrations C_(aliphat.) --H

References:

US5994561,1999,A