Acetone → 1H-Pyrrole-2,5-dione, 1,1'-(4-methyl-1,3-phenylene)bis-

HRID 262418Notes

Reaction equation

[C:1]1(=[O:7])O[C:4](=[O:5])[CH:3]=[CH:2]1.[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:10]=1[NH2:16].O.O.O.O.O.O.[Cl-].[Mg+2].[Cl-].C(O[C:30](=[O:32])[CH3:31])(=O)C.[CH3:33][C:34](C)=[O:35]>O.C(N(CC)CC)C>[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:30](=[O:32])[CH:31]=[CH:33][C:34]2=[O:35])=[CH:11][C:10]=1[N:16]1[C:1](=[O:7])[CH:2]=[CH:3][C:4]1=[O:5]

Participants

Conditions

Temperature: 40 °C

Procedure

A flask was equipped as in Example 1. To a solution of maleic anhydride (1.7 parts) in 3.9 parts acetone was added a solution of 1 part 4-methyl-m-phenylenediamine, 0.28 part triethylamine and 2.5 parts acetone. The heterogeneous reaction mixture was stirred at 40° C. for 30 minutes. Magnesium chloride hexahydrate (0.071 part) and 2.16 part acetic anhydride were added all at once. The reaction temperature was raised to 50° C. and maintained for 2.5 hours. Thirty minutes after the addition the mixture became homogeneous and remained so. The solution was cooled, and 16 parts water was added; the precipitated product was filtered by vacuum filtration, washed with water, and dried in a vacuum oven at 60° C. for 24 hours. N,N'-(4-Methyl-m-phenylene)dimaleimide, m.p. 168°-172° C., was obtained in 85% yield.

Workup

customA flask was equipped as in Example 1
temperatureThe reaction temperature was raised to 50° C.
temperaturemaintained for 2.5 hours
additionThirty minutes after the addition the mixture
temperatureThe solution was cooled
filtrationthe precipitated product was filtered by vacuum filtration
washwashed with water
customdried in a vacuum oven at 60° C. for 24 hours

Sources & evidence

ORD record: ord-42c1bcf76c544651a422c1274a989376
Source dataset: uspto-grants-1979_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04154737

Reaction notes

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