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

HRID 262422

Reaction equation

HRID 262422 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.[C:32](OCC)(=[O:34])[CH3:33]>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:33][C:32]2=[O:34])[CH:9]=1

Participants

7

Reactant 5

HCID 7918Acetic AnhydrideHCID 7923Maleic AnhydrideHCID 7935M-PhenylenediamineHCID 8857Ethyl Acetate2×HCID 24644Magnesium chloride hexahydrate

Product 1

HCID 18156N,N'-1,3-PhenylenedimaleimideYield 70%

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) and 13 parts ethyl acetate was added a mixture of 1 part m-phenylenediamine, 0.32 part triethylamine and 2.3 parts ethyl acetate over a 40-minute period. The resulting heterogeneous mixture was maintained at 40° C. for 50 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. The precipitated product was isolated by vacuum filtration, the filter cake washed with water, and dried. A 70% yield of N,N'-m-phenylenedimaleimide, m.p. 202°-203° C., was obtained.

Workup

  1. customA flask was equipped as in Example 1
  2. temperatureThe temperature was raised to 50° C.
  3. temperaturemaintained for 3 hours
  4. customThe precipitated product was isolated by vacuum filtration
  5. washthe filter cake washed with water
  6. customdried

Sources & evidence

ORD record
ord-5e0455b409cc41cca73ffadc3173a841
Source dataset
uspto-grants-1979_05
Patent number
US04154737

Linked notes

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