Acetic Anhydride → 1H-Pyrrole-2,5-dione, 1-dodecyl-

HRID 2286386Notes

Reaction equation

HRID 2286386 reaction equation
[C:1]1(=[O:7])O[C:4](=[O:5])[CH:3]=[CH:2]1.[CH2:8]([NH2:20])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].C(OC(=O)C)(=O)C.C(N(CC)CC)C>C([O-])(=O)C.[Ni+2].C([O-])(=O)C.O.CN(C)C=O>[CH2:8]([N:20]1[C:4](=[O:5])[CH:3]=[CH:2][C:1]1=[O:7])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

8

Reactant 4

HCID 7918Acetic AnhydrideHCID 7923Maleic Anhydride2×HCID 8471TriethylamineHCID 13583Dodecylamine3×

Product 1

HCID 871911H-Pyrrole-2,5-dione, 1-dodecyl-

Reagents, catalysts & solvents 3

HCID 9756Nickel AcetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

1 Mole of maleic anhydride and 300 g of dimethylformamide were charged into a 2-liter three-necked flask and stirred to dissolve the maleic anhydride into the dimethylformamide. To the resulting solution were added, with stirring, 1.02 moles of laurylamine over a period of 30 minutes while cooling the flask in a cold water bath. The exothermic reaction occurred simultaneously with the addition of the laurylamine which was, therefore, so carefully done that the temperature of the reaction mixture could be maintained at around 50° C. Immediately after completion of the addition of the laurylamine, the bath temperature was increased to 50° C. at which the stirring was continued for 1 hour. After completion of the amide-formation reaction, 1.6 moles of acetic anhydride, 0.016 mole of nickel acetate and 0.16 mole of triethylamine were added, with stirring, to the reaction mixture. The resulting mixture was heated to 90°-95° C. at which the stirring was continued for 1.5 hours to effect the dehydration reaction. Subsequently, the reaction mixture was cooled to room temperature and poured into ice and water to yield a precipitate. The precipitate was collected by filtration, washed with water, neutralized with sodium carbonate and recrystallized twice from water-containing ethanol (90%) to obtain white crystals of N-laurylmaleimide having a melting point of 56° C.

Workup

  1. additionTo the resulting solution were added
  2. stirringwith stirring
  3. customThe exothermic reaction
  4. temperaturethe bath temperature was increased to 50° C. at which the stirring
  5. additionwere added
  6. stirringwith stirring, to the reaction mixture
  7. temperatureThe resulting mixture was heated to 90°-95° C. at which the stirring
  8. waitwas continued for 1.5 hours
  9. customthe dehydration reaction
  10. temperatureSubsequently, the reaction mixture was cooled to room temperature
  11. customto yield a precipitate
  12. filtrationThe precipitate was collected by filtration
  13. washwashed with water
  14. customrecrystallized twice from water-
  15. additioncontaining ethanol (90%)

Sources & evidence

ORD record
ord-b6d4fda9427d41fb8ee672399d0d7edc
Source dataset
uspto-grants-1981_05
Patent number
US04266005

Reaction notes

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