Maleic Anhydride → HCID 86738811, compound

HRID 354642Notes

Reaction equation

HRID 354642 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[CH:17][C:18]([C:21]2[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=2)([CH3:20])[CH3:19])[CH3:16])=[CH:11][CH:10]=1>CC(C)=O>[CH3:16][C:15]([C:12]1[CH:11]=[CH:10][C:9]([NH:8][C:1](=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5])=[CH:14][CH:13]=1)=[CH:17][C:18]([CH3:20])([CH3:19])[C:21]1[CH:22]=[CH:23][C:24]([NH:27][C:1](=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5])=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 536459434,4'-(4-Methylpent-2-ene-2,4-diyl)dianiline

Product 1

HCID 86738811HCID 86738811, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Maleic anhydride (43 g) was dissolved in 250 ml of acetone. While this solution was being kept at 18° C., 53 g of 2,4-di(p-amino-phenyl)-4-methyl-2-pentene was slowly added thereto with stirring. The resulting reaction mixture was stirred at 18° C. for 21/2 hours to form N,N'-(1-methyl-3,3-dimethyl-1-propenylenedi-p-phenylene)bismaleamic acid having the formula ##STR20## At this time, the reaction mixture was a yellow slurry. Then, 0.5 g of cobalt acetate tetrahydrate, 10 g of triethylamine, and 50 g of acetic anhydride were added, with stirring, to the above slurry. After completion of the addition, the slurry was heated to 61° C. and stirred at that temperature for 8 hours, so that it became a clear brown solution. This solution was cooled to room temperature and, thereafter, worked up in the same manner as described in Example 1. However, the amount of methyl alcohol added to the solution was 80 ml and the amount of water into which the solution was poured was 7,000 ml. As a result, there was obtained 80 g of product melting at 99°-110° C. Its yield was 94% based on the amount of diamine used as the starting material. It was confirmed by infrared absorption spectroscopy, nuclear magnetic resonance spectroscopy, and elemental analysis that the product was N,N'-(1-methyl-3,3-dimethyl-1-propenylenedi-p-phenylene)bismaleimide having the formula ##STR21##

Workup

  1. customwas being kept at 18° C.
  2. customThe resulting reaction mixture
  3. stirringwas stirred at 18° C. for 21/2 hours

Sources & evidence

ORD record
ord-c5cab59bd164435b942ed6e6bccaf23e
Source dataset
uspto-grants-1983_03
Patent number
US04376206

Reaction notes

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