Dimethylmaleic anhydride → 3,5-Bis-(dimethylmaleimidyl)-phthalic anhydride

HRID 46604

Reaktionsgleichung

Reaktionsgleichung von HRID 46604
[NH2:1][C:2]1[CH:10]=[C:9]([NH2:11])[CH:8]=[C:4]([C:5]([O-:7])=O)[C:3]=1[C:12]([O-:14])=[O:13].[Na+].[Na+].[CH3:17][C:18]1=[C:19]([CH3:25])[C:20]([O:22][C:23]1=[O:24])=O>O.C1(C)C=CC=CC=1>[CH3:25][C:19]1[C:20](=[O:22])[N:1]([C:2]2[CH:10]=[C:9]([N:11]3[C:5](=[O:7])[C:4]([CH3:8])=[C:3]([CH3:2])[C:12]3=[O:13])[CH:8]=[C:4]3[C:5]([O:14][C:12](=[O:13])[C:3]=23)=[O:7])[C:23](=[O:24])[C:18]=1[CH3:17]

Komponenten

5

Edukt 2

HCID 13010Dimethylmaleic anhydrideHCID 20346778Disodium 3,5-diaminophthalate

Produkt 1

HCID 539736833,5-Bis-(dimethylmaleimidyl)-phthalic anhydrideAusbeute 115,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

7.20 g (0.039 mol) of disodium 3,5-diaminophthalate, dissolved in 200 ml of water, are added to a solution of 8.82 g (0.078 mol) of dimethylmaleic anhydride in 80 ml of toluene. This mixture is boiled under reflux for 1 hour. It is then evaporated to dryness in a rotary evaporator, the residue is dissolved, at 90° C., in 100 ml of N,N-dimethylacetamide and 50 ml of water and the solution is rendered acid to Congo Blue with 10% strength hydrochloric acid. After cooling, the slurry-like mixture is filtered and the residue is rinsed with acetone and then dried in vacuo at 80° C. The dry residue is then suspended in 100 ml of acetic anhydride and this mixture is warmed to about 100° C. for 1 hour. It is then evaporated to dryness and the residue is recrystallised from 1,2-dichlorobenzene. 8.9 g (69% of theory) of 3,5-bis-(dimethylmaleimidyl)-phthalic anhydride are obtained; colour: light brownish; melting point 298° C. (decomposition).

Aufarbeitung

  1. temperatureunder reflux for 1 hour
  2. customIt is then evaporated to dryness in a rotary evaporator
  3. dissolutionthe residue is dissolved, at 90° C., in 100 ml of N,N-dimethylacetamide
  4. temperatureAfter cooling
  5. filtrationthe slurry-like mixture is filtered
  6. washthe residue is rinsed with acetone
  7. customdried in vacuo at 80° C
  8. customIt is then evaporated to dryness
  9. customthe residue is recrystallised from 1,2-dichlorobenzene

Quellen und Nachweise

ORD-Eintrag
ord-31ac854078dd47d5a35fc2cb1eaee9ab
Quelldatensatz
uspto-grants-1979_11
Patentnummer
US04174326

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