O-Xylene → N-Nonylmaleimide

HRID 1587638Notes

Reaction equation

HRID 1587638 reaction equation
[C:1]1(=[O:7])O[C:4](=[O:5])[CH:3]=[CH:2]1.[CH2:8]([NH2:17])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C1(C)C(C)=CC=CC=1>O>[CH2:8]([N:17]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][CH3:16]

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 7923Maleic AnhydrideHCID 16215Nonylamine

Product 1

HCID 512831N-Nonylmaleimide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
120 °C

Procedure

One equivalent each of maleic anhydride and n-nonylamine are charged into a 1 liter 3-neck round bottom glass flask containing 300 ml xylene, a reflux condenser with a Dean-Stark attachment, Teflon-coated magnetic stirring bar, and a thermometer. The contents are heated to 120° C. for about 15 hours, the reaction extent being monitored by the amount of water collected. After 1 equivalent of water is collected, the reaction solvent is flash distilled off. The absence of an infrared absorbance at 1830 cm-1 and 1791 cm-1 is evidence of anhydride consumption; the presence of an infrared absorbance at 1772 cm-1 is evidence of imide formation.

Workup

  1. customcollected
  2. distillationdistilled off
  3. customevidence of anhydride consumption

Sources & evidence

ORD record
ord-53207747640a46d19bb27ff1d7f530cd
Source dataset
uspto-grants-1993_06
Patent number
US05219482

Reaction notes

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