Maleic Anhydride → HCID 18995300, compound

HRID 375415Notes

Reaction equation

HRID 375415 reaction equation
[C:1]1(=[O:7])O[C:4](=[O:5])[CH:3]=[CH:2]1.[NH2:8][C:9]1[CH:10]=[C:11]([CH:45]=[CH:46][CH:47]=1)[O:12][C:13]1[CH:44]=[CH:43][C:16]([C:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([CH3:42])([CH3:41])[C:27]3[CH:32]=[CH:31][C:30]([O:33][C:34]4[CH:39]=[CH:38][CH:37]=[C:36]([NH2:40])[CH:35]=4)=[CH:29][CH:28]=3)=[CH:22][CH:21]=2)([CH3:19])[CH3:18])=[CH:15][CH:14]=1>C1(C)C(C)=CC=CC=1.CN(C)C=O.P(=O)(O)(O)O>[C:1]1(=[O:7])[N:40]([C:36]2[CH:35]=[C:34]([CH:39]=[CH:38][CH:37]=2)[O:33][C:30]2[CH:31]=[CH:32][C:27]([C:26]([C:23]3[CH:22]=[CH:21][C:20]([C:17]([CH3:19])([CH3:18])[C:16]4[CH:15]=[CH:14][C:13]([O:12][C:11]5[CH:45]=[CH:46][CH:47]=[C:9]([N:8]6[C:1](=[O:7])[CH:2]=[CH:3][C:4]6=[O:5])[CH:10]=5)=[CH:44][CH:43]=4)=[CH:25][CH:24]=3)([CH3:42])[CH3:41])=[CH:28][CH:29]=2)[C:4](=[O:5])[CH:3]=[CH:2]1

Participants

6

Reactant 2

HCID 7923Maleic AnhydrideHCID 15217322HCID 15217322, compound

Product 1

HCID 18995300HCID 18995300, compoundYield 97.4%

Reagents, catalysts & solvents 3

HCID 1004Phosphoric AcidCatalystHCID 6228DimethylformamideSolventHCID 7237O-XyleneSolvent2×

Procedure

In the same reactor used in Example 2D, there were placed 26.5 g (0.27 mole) of maleic anhydride, 0.7 g of phosphoric acid and 150 ml of mixed xylene. A solution was then added dropwise thereto, the solution having been prepared by thermally dissolving 52.8 g (0.1 mole) of 1,4-bis[4-(3-aminophenoxy)-α,α-dimethylbenzyl]benzene obtained in Example 1D in a mixture of 100 ml of mixed xylene and 50 ml of N,N-dimethylformamide. A dropping time of 5 hours and an aging time of 2 hours were used in order to carry out the reaction. The reaction solution was concentrated to about 1/2 the original amount and then cooled. When a temperature of 80° C. had been reached, 50 g of water was added thereto. Afterward, the solution was slowly cooled, so that crystals precipitated. The precipitated crystals were then cooled to room temperatures filtered; and washed with cold methanol. 67.1 g of desired crude 1,4-bis[4-(3-maleimidophenoxy)-α,α-dimethylbenzyl]benzene was obtained.

Workup

  1. additionA solution was then added dropwise
  2. customthe solution having been prepared
  3. customA dropping time of 5 hours
  4. customan aging time of 2 hours
  5. customthe reaction
  6. concentrationThe reaction solution was concentrated to about 1/2 the original amount
  7. temperaturecooled
  8. customa temperature of 80° C.
  9. addition50 g of water was added
  10. temperatureAfterward, the solution was slowly cooled, so that crystals
  11. customprecipitated
  12. temperatureThe precipitated crystals were then cooled to room temperatures
  13. filtrationfiltered
  14. washand washed with cold methanol

Sources & evidence

ORD record
ord-d860950201214c20ada24a18949842dd
Source dataset
uspto-grants-1996_01
Patent number
US05484948

Reaction notes

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