Reaction #1528381

Reaction equation

dimethylmaleic anhydride

p-aminobenzoic acid

sodium acetate

acetic anhydride

→

N-(p-carboxyphenyl)dimethylmaleimide

Solvents

acetone

Conditions

Workup

1. 1
   Otherto obtain a yellow precipitate
2. 2
   FiltrationThereafter, the precipitate was collected by filtration under reduced pressure
3. 3
   Otherrecrystallized from a solution of DMF/water (50:50 (w/w))
4. 4
   Otherto give an intermediate
5. 5
   Otherplaced in an ice bath
6. 6
   Otherto obtain a precipitate
7. 7
   FiltrationThe precipitate was collected by filtration under reduced pressure
8. 8
   Otherrecrystallized from a solution of ethanol/water (50:50 (w/w))

Procedure

37.8 g (0.3 mol) of dimethylmaleic anhydride was slowly added to a solution of 41.1 g (0.3 mol) of p-aminobenzoic acid and 300 ml of acetone in a 250 ml flask at 10° C. The mixture was stirred for 2 hours to obtain a yellow precipitate. Thereafter, the precipitate was collected by filtration under reduced pressure and recrystallized from a solution of DMF/water (50:50 (w/w)) to give an intermediate. The intermediate was treated with sodium acetate and acetic anhydride at 85° C. for 4 hours, cooled to room temperature, and placed in an ice bath to obtain a precipitate. The precipitate was collected by filtration under reduced pressure and recrystallized from a solution of ethanol/water (50:50 (w/w)) to give N-(p-carboxyphenyl)dimethylmaleimide.

Source