Acetone → Ethylenebismaleimide

HRID 262419Notes

Reaction equation

HRID 262419 reaction equation
[C:1]1(=[O:7])O[C:4](=[O:5])[CH:3]=[CH:2]1.[CH2:8]([NH2:11])[CH2:9][NH2:10].O.O.O.O.O.O.[Cl-].[Mg+2].[Cl-].C(O[C:25](=[O:27])[CH3:26])(=O)C.[CH3:28][C:29](C)=[O:30]>O.C(N(CC)CC)C>[CH2:8]([N:11]1[C:1](=[O:7])[CH:2]=[CH:3][C:4]1=[O:5])[CH2:9][N:10]1[C:25](=[O:27])[CH:26]=[CH:28][C:29]1=[O:30]

Participants

8

Reactant 5

HCID 180Acetone2×HCID 3301EthylenediamineHCID 7918Acetic AnhydrideHCID 7923Maleic AnhydrideHCID 24644Magnesium chloride hexahydrate

Product 1

HCID 237509EthylenebismaleimideYield 27%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
40 °C

Procedure

A flask was equipped as in Example 1. To a solution of maleic anhydride (3.64 parts) in 10.6 parts acetone was added a solution of 1 part ethylenediamine, 0.61 part triethylamine and 1.5 parts acetone over a 25-minute period. The resulting reaction mixture contained white solids and was maintained at 40° C. for 30 minutes. Magnesium chloride hexahydrate (0.15 part) and 4.6 parts acetic anhydride were added all at once. The reaction temperature was raised to 50° C. and held there for 2.5 hours. The homogeneous reaction mixture was cooled and 25 parts water added. The precipitated product was filtered by vacuum filtration, washed with water, and dried in a vacuum oven. A 27% yield of N,N'-ethylenedimaleimide, m.p. 193°-194° C., was obtained.

Workup

  1. customA flask was equipped as in Example 1
  2. customThe resulting reaction mixture
  3. temperatureThe reaction temperature was raised to 50° C.
  4. temperatureThe homogeneous reaction mixture was cooled
  5. filtrationThe precipitated product was filtered by vacuum filtration
  6. washwashed with water
  7. customdried in a vacuum oven

Sources & evidence

ORD record
ord-4e1c03fd2c6f454490ca464d71c987bf
Source dataset
uspto-grants-1979_05
Patent number
US04154737

Reaction notes

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