Acetic Anhydride → N,N'-1,3-Phenylenedimaleimide

HRID 262416Notes

Reaction equation

HRID 262416 reaction equation
[C:1]1(=[O:7])O[C:4](=[O:5])[CH:3]=[CH:2]1.[C:8]1([NH2:15])[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[CH:9]=1.C(O[C:20](=[O:22])[CH3:21])(=O)C.O.O.O.O.[C:27]([O-])(=[O:29])[CH3:28].[Mg+2].C([O-])(=O)C>O.C(N(CC)CC)C.CC(C)=O>[C:8]1([N:15]2[C:1](=[O:7])[CH:2]=[CH:3][C:4]2=[O:5])[CH:13]=[CH:12][CH:11]=[C:10]([N:14]2[C:20](=[O:22])[CH:21]=[CH:28][C:27]2=[O:29])[CH:9]=1

Participants

8

Reactant 4

HCID 7918Acetic AnhydrideHCID 7923Maleic AnhydrideHCID 7935M-PhenylenediamineHCID 134717Magnesium Acetate Tetrahydrate

Product 1

HCID 18156N,N'-1,3-PhenylenedimaleimideYield 74%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
40 °C

Procedure

A glass flask was equipped with a thermometer, mechanical paddle stirrer and a water cooled condenser. Crushed maleic anhydride (1.92 parts) was added to a solution of 1 part m-phenylenediamine and 13 parts acetone over a 15-minute period. The heterogeneous reaction mixture was stirred at 40° C. for 1 hour. Acetic anhydride (2.44 parts), 0.32 part triethylamine, and 0.04 part magnesium acetate tetrahydrate were added all at once. The temperature was raised to 60° C. using a heating mantle and maintained for 4 hours. The reaction mixture was cooled, 20 parts water added, and the precipitated product isolated by filtration using a vacuum filter funnel. The filter cake was washed with water and dried for 24 hours at 60°-70° C. in a vacuum oven. A 74% yield of N,N'-m-phenylenedimaleimide, m.p. 203°-204° C. was obtained.

Workup

  1. customA glass flask was equipped with a thermometer, mechanical paddle stirrer and a water cooled condenser
  2. temperatureThe temperature was raised to 60° C.
  3. temperaturemaintained for 4 hours
  4. temperatureThe reaction mixture was cooled
  5. customthe precipitated product isolated by filtration
  6. filtrationfilter funnel
  7. washThe filter cake was washed with water
  8. customdried for 24 hours at 60°-70° C. in a vacuum oven

Sources & evidence

ORD record
ord-d49528e09a13439fb3a974f003572bf3
Source dataset
uspto-grants-1979_05
Patent number
US04154737

Reaction notes

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