Dichloromaleic anhydride → 3-(2',3'-Dichloromaleinimidyl)-phthalic anhydride

HRID 971454Notes

Reaction equation

HRID 971454 reaction equation
[Cl:1][C:2]1[C:3]([O:5][C:6](=O)[C:7]=1[Cl:8])=[O:4].[NH2:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:13]([C:14]([OH:16])=O)[C:12]=1[C:20]([OH:22])=[O:21]>O1CCOCC1>[Cl:1][C:2]1[C:3]([N:10]([C:11]2[CH:19]=[CH:18][CH:17]=[C:13]3[C:14]([O:22][C:20](=[O:21])[C:12]=23)=[O:16])[C:6](=[O:5])[C:7]=1[Cl:8])=[O:4]

Participants

4

Reactant 2

HCID 70728Dichloromaleic anhydrideHCID 794903-Aminophthalic acid

Product 1

HCID 544274933-(2',3'-Dichloromaleinimidyl)-phthalic anhydrideYield 58%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

20 g (0.12 mol) of 2,3-dichloromaleic anhydride are added to a solution of 18.1 g (0.1 mol) of 3-aminophthalic acid in 90 ml of dioxane. The reaction mixture is stirred at 20°-30° C., whereupon a clear solution is produced over the course of approx. 30 minutes. The dioxane is then distilled off in vacuo (20 mm Hg) and the oil which remains is warmed to 130° C. After 3 hours, the crystalline mass is cooled to 50° C. and mixed with 100 ml of ethyl acetate. The reaction product is filtered off at 10° C. and dried in vacuo at 80° C. 18.1 g (58% of theory) of crystalline 3-(2',3'-dichloromaleinimidyl)-phthalic anhydride are obtained, melting at 229°-230° C. after recrystallisation from anhydrous acetic acid.

Workup

  1. customis produced over the course of approx. 30 minutes
  2. distillationThe dioxane is then distilled off in vacuo (20 mm Hg)
  3. temperaturethe crystalline mass is cooled to 50° C.
  4. additionmixed with 100 ml of ethyl acetate
  5. filtrationThe reaction product is filtered off at 10° C.
  6. customdried in vacuo at 80° C

Sources & evidence

ORD record
ord-84befe9e196f415c9c6d094ff9d42414
Source dataset
uspto-grants-1979_07
Patent number
US04160081

Reaction notes

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