Toluene → 5,5'-Carbonyldi(2-benzofuran-1,3-dione)--1-(4-aminophenyl)-1,3,3-trimethyl-2,3-dihydro-1H-inden-5-amine (1/1)

HRID 1975228Notes

Reaction equation

HRID 1975228 reaction equation
[CH:1]1[C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]3[C:15]([O:17][C:18](=[O:19])[C:11]=3[CH:10]=2)=[O:16])=[O:8])=[CH:5][C:4]2[C:20]([O:22][C:23](=[O:24])[C:3]=2[CH:2]=1)=[O:21].[NH2:25]C1C=C(C(F)(F)F)C=C(N)N=1.N[C:38]1C=[C:42](N)[CH:41]=[CH:40][C:39]=1[CH3:45].[C:46]1([CH3:52])C=CC=CC=1.C[N:54]1[CH2:58][CH2:57][CH2:56][C:55]1=O>O>[CH3:45][C:39]1([CH3:38])[C:56]2[CH:57]=[C:58]([NH2:54])[CH:46]=[CH:52][C:55]=2[C:41]([C:6]2[CH:1]=[CH:2][C:3]([NH2:25])=[CH:4][CH:5]=2)([CH3:42])[CH2:40]1.[CH:1]1[C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]3[C:15]([O:17][C:18](=[O:19])[C:11]=3[CH:10]=2)=[O:16])=[O:8])=[CH:5][C:4]2[C:20]([O:22][C:23](=[O:24])[C:3]=2[CH:2]=1)=[O:21]

Participants

7

Reactant 5

HCID 1140TolueneHCID 72612,4-DiaminotolueneHCID 13387N-methyl-2-pyrrolidoneHCID 754984,4'-Carbonyldiphthalic anhydrideHCID 218962064-(Trifluoromethyl)pyridine-2,6-diamine

Product 1

HCID 64544855,5'-Carbonyldi(2-benzofuran-1,3-dione)--1-(4-aminophenyl)-1,3,3-trimethyl-2,3-dihydro-1H-inden-5-amine (1/1)

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

32.22 g (0.1 mole) of 3,3',4,4'-benzophenonetetracarboxylic acid dianhydride was dissolved in 240 g of N-methyl-2-pyrrolidone in a four-necked separable flask provided with a thermometer, a stirrer, a raw material inlet and a dry nitrogen gas-introducing tube. Thereto were added 10.63 g (0.06 mole) of 2,6-diamino-4-trifluoromethylpyridine and 4.88 g (0.04 mole) of 2,4-diaminotoluene. The system was stirred for 5 hours at 20° C. to complete the reaction. During the period, dry nitrogen was continuously blown. Subsequently, 72 g of toluene was added thereto. The dry nitrogen gas-introducing tube was removed, and instead a Dean Stark reflux condenser was fitted. The ice bath was removed and the system was heated using an oil bath. The heating was continued to allow imidization to proceed at 140°-150° C. while the water generated by imidization was discharged out of the system by azeotropy with toluene. After 5 hours water generation was over, and the imidization reaction was stopped. The resulting polyimide varnish was dropwise added to 30 liters of pure water in 1 hour with stirring, to precipitate a resin. Filtration was conducted to recover a solid content. The solid was dried in a drier at 120° C. for 3 hours to obtain a polyimide resin. The polyimide resin was measured for FT-IR spectrum to determine its imidization degree from (a) an absorption of amide bond before imidization, appearing at 1650 cm-1 and (b) an absorption of imide ring, appearing at 1780 cm-1. As a result, the imidization degree was 100%.

Workup

  1. customprovided with a thermometer, a stirrer
  2. customthe reaction
  3. customThe dry nitrogen gas-introducing tube was removed
  4. temperatureinstead a Dean Stark reflux condenser
  5. customwas fitted
  6. customThe ice bath was removed
  7. temperaturethe system was heated
  8. customto proceed at 140°-150° C. while the water
  9. waitAfter 5 hours water generation was
  10. customover, and the imidization reaction
  11. stirringwith stirring
  12. customto precipitate a resin
  13. filtrationFiltration
  14. customto recover a solid content
  15. customThe solid was dried in a drier at 120° C. for 3 hours

Sources & evidence

ORD record
ord-f632c33f99ae49ad9ac767cfecccaf45
Source dataset
uspto-grants-1994_02
Patent number
US05284899

Reaction notes

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