Maleic Anhydride → N,N-Diallylmaleamic acid

HRID 1154516Notes

Reaction equation

HRID 1154516 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[CH2:8]([NH:11][CH2:12][CH:13]=[CH2:14])[CH:9]=[CH2:10].[13CH4]>C1(C)C=CC=CC=1>[CH2:8]([N:11]([CH2:12][CH:13]=[CH2:14])[C:1](=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5])[CH:9]=[CH2:10]

Participants

5

Reactant 3

HCID 7923Maleic AnhydrideHCID 31279DiallylamineHCID 105026Carbon-13C

Product 1

HCID 59084702N,N-Diallylmaleamic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Maleic anhydride (100 g, 1.02 mol) was dispersed in 400 mL toluene at 40° C. Diallylamine (97% pure, 100 g, 1.00 mol) was added over a period of 30 minutes with cooling so that the reaction temperature was maintained below 40° C. After addition, the reaction mixture was stirred at room temperature for 3 hours. The IR of the reaction mixture showed the absence of the anhydride. A nearly quantitative conversion was obtained. The Carbon-13 data is shown in Table 1.

Workup

  1. temperaturewith cooling so that the reaction temperature
  2. temperaturewas maintained below 40° C
  3. additionAfter addition
  4. customA nearly quantitative conversion was obtained

Sources & evidence

ORD record
ord-cedffab8b1984b41a69052753d5aa488
Source dataset
uspto-grants-1984_12
Patent number
US04490308

Reaction notes

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