Acetone → N,N'-1,3-Phenylenedimaleimide

HRID 262417Notes

Reaction equation

HRID 262417 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.O.O.O.O.O.O.[Cl-].[Mg+2].[Cl-].C(O[C:29](=[O:31])[CH3:30])(=O)C.[CH3:32][C:33](C)=[O:34]>C(N(CC)CC)C>[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:29](=[O:31])[CH:30]=[CH:32][C:33]2=[O:34])[CH:9]=1

Participants

7

Reactant 5

HCID 180Acetone2×HCID 7918Acetic AnhydrideHCID 7923Maleic AnhydrideHCID 7935M-PhenylenediamineHCID 24644Magnesium chloride hexahydrate

Product 1

HCID 18156N,N'-1,3-PhenylenedimaleimideYield 92%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
40 °C

Procedure

A flask was equipped as in Example 1. To a solution of maleic anhydride (1.92 parts) in 4.8 parts acetone was added a solution of 1 part m-phenylenediamine, 0.32 part triethylamine and 1.6 parts acetone over a 15-minute period. A precipitate formed during that time. The heterogeneous reaction mixture was maintained at 40° C. for 30 minutes. Magnesium chloride hexahydrate (0.08 part) and 2.44 parts acetic anhydride were added all at once. The temperature was raised to 50° C. and maintained for 3 hours. After 30 minutes, the reaction mixture became homogeneous and amber in color. Five minutes later, the product began to precipitate. At the end of the reaction time, the mixture was cooled and 12 parts water added. The precipitated product was collected by vacuum filtration, washed with water, and dried for 24 hours at 60° C. in a vacuum oven. A 92% yield of N,N'-m-phenylenedimaleimide, m.p. 204°-205° C., was obtained.

Workup

  1. customA flask was equipped as in Example 1
  2. customA precipitate formed during that time
  3. temperatureThe temperature was raised to 50° C.
  4. temperaturemaintained for 3 hours
  5. customFive minutes
  6. customto precipitate
  7. temperatureAt the end of the reaction time, the mixture was cooled
  8. addition12 parts water added
  9. filtrationThe precipitated product was collected by vacuum filtration
  10. washwashed with water
  11. customdried for 24 hours at 60° C. in a vacuum oven

Sources & evidence

ORD record
ord-dab1331b97f54aa09ed037a702a64e79
Source dataset
uspto-grants-1979_05
Patent number
US04154737

Reaction notes

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