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

HRID 66255

Reaction equation

HRID 66255 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 to 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-89c5e3339af441f5ad92c6c3e237f56e
Source dataset
uspto-grants-1978_12
Patent number
US04131613

Linked notes

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