P-Phenylenediamine → HCID 12422004, compound

HRID 236388Notes

Reaction equation

HRID 236388 reaction equation
[Cl:1][C:2]1[C:3]([Cl:15])=[C:4]([Cl:14])[C:5]([Cl:13])=[C:6]2[C:11](=[O:12])O[C:8](=[O:9])[C:7]=12.[CH:16]1[C:21]([NH2:22])=[CH:20][CH:19]=[C:18]([NH2:23])[CH:17]=1>CN1CCCC1=O>[C:18]1([N:23]2[C:8](=[O:9])[C:7]3=[C:2]([Cl:1])[C:3]([Cl:15])=[C:4]([Cl:14])[C:5]([Cl:13])=[C:6]3[C:11]2=[O:12])[CH:19]=[CH:20][C:21]([N:22]2[C:11](=[O:12])[C:6]3=[C:5]([Cl:13])[C:4]([Cl:14])=[C:3]([Cl:15])[C:2]([Cl:1])=[C:7]3[C:8]2=[O:9])=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 7814P-PhenylenediamineHCID 8326Tetrachlorophthalic anhydride

Product 1

HCID 12422004HCID 12422004, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
200 °C

Procedure

In a 5 liter round-bottom flask equipped with a heating mantle, a stirrer, a thermometer, a condenser and a nitrogen purge, there were reacted 457.5 gms (1.6 mole) of tetrachlorophthalic anhydride and 86.5 gms (0.8 mole) of p-phenylenediamine in 2000 ml. of N-methyl-2-pyrrolidone (NMP), the reactants going into solution as the mixture was heated with stirring. At 170° C., precipitation began and continued as the temperature was raised to 200° C. where it was maintained for 90 minutes. The reaction mixture was then allowed to cool overnight. The cooled mixture was filtered and the yellow precipitate was recovered. The precipitate was washed with NMP, thoroughly stirred in acetone, filtered and washed with more acetone. The product was dried under vacuum at 150° C. for 16 hours. 272.7 gms (yield=53%) of an ivory-yellow material was obtained, having a melting point in excess of 500° C., with one sublimation at about 425° C. The IR spectrum had the characteristics of an imide with the absorption bands at 1710s and 1770w cm-1. The product was insoluble in water.

Workup

  1. customIn a 5 liter round-bottom flask equipped with a heating mantle, a stirrer
  2. customa thermometer, a condenser and a nitrogen purge
  3. temperaturewas heated
  4. customAt 170° C., precipitation
  5. temperaturewas maintained for 90 minutes
  6. temperatureto cool overnight
  7. filtrationThe cooled mixture was filtered
  8. customthe yellow precipitate was recovered
  9. washThe precipitate was washed with NMP
  10. stirringthoroughly stirred in acetone
  11. filtrationfiltered
  12. washwashed with more acetone
  13. customThe product was dried under vacuum at 150° C. for 16 hours

Sources & evidence

ORD record
ord-2e06becd8b5e4b2ca3dbc3338ea8503b
Source dataset
uspto-grants-1987_02
Patent number
US04644066

Reaction notes

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