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 1371238

Reaction equation

HRID 1371238 reaction equation
NC1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([NH2:16])[CH:10]=2)[CH:5]=[CH:6][C:7]=1O.C[N:18]1[CH2:22][CH2:21][CH2:20][C:19]1=[O:23].[CH:24]1C(O[C:31]2[CH:36]=[CH:35][C:34]3[C:37]([O:39][C:40](=[O:41])[C:33]=3[CH:32]=2)=[O:38])=CC2C(OC(=O)C=2[CH:25]=1)=O.[C:47]1(C)C=CC=CC=1.[CH3:54][OH:55].[OH2:56]>>[CH3:47][C:4]1([CH3:3])[C:9]2[CH:10]=[C:11]([NH2:16])[CH:12]=[CH:13][C:14]=2[C:6]([C:19]2[CH:20]=[CH:21][C:22]([NH2:18])=[CH:25][CH:24]=2)([CH3:7])[CH2:5]1.[CH:9]1[C:20]([C:19]([C:36]2[CH:31]=[CH:32][C:33]3[C:40]([O:39][C:37](=[O:38])[C:34]=3[CH:35]=2)=[O:41])=[O:23])=[CH:21][C:22]2[C:54]([O:56][C:12](=[O:15])[C:13]=2[CH:14]=1)=[O:55]

Participants

6

Reactant 5

HCID 1140TolueneHCID 13387N-methyl-2-pyrrolidoneHCID 745744,4'-Oxydiphthalic anhydrideHCID 6122943,3'-Diamino-[1,1'-biphenyl]-4,4'-diolHCID 22242641Methanol--water (1/1)

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)

Procedure

3,3′-diamino-4,4′-dihydroxybiphenyl (13.0 g) and 74.2 g of NMP were sequentially charged into a 1 L round-bottom flask. The mixture was stirred until it was completely dissolved. While maintaining the flask at room temperature, 14.9 g of ODPA was added slowly. After the resulting mixture was stirred at room temperature for 2 hours, 3.9 g of NDA was added to the flask. After the resulting mixture was stirred at room temperature for 16 hours, 16 g of toluene was added to the flask. Using a Dean-Stark distillation equipment, the reaction solution was refluxed at 140° C. for 3 hours to complete the reaction. The reaction solution thus prepared was allowed to cool to room temperature, and slowly poured into a 1:4 methanol-water mixture to obtain precipitates. The precipitates were filtered and dried in a vacuum drying oven at 40° C. for one day. 19.6 g of the soluble polyimide resin thus obtained in a powder form was charged into a 1 L round-bottom flask and dissolved in 100 g of N-methyl-2-pyrrolidone (NMP). The resulting solution was cooled on ice and then 2.12 g of triethylamine (TEA) was added thereto, maintaining the temperature at 0˜5° C. After stirring for 10 minutes, 2.27 g of chloromethylethylether was slowly added to the solution. After the resulting solution was stirred for 3 hours while maintaining it at a low temperature, triethylammonium chloride salt was filtered off. The filtrate was slowly poured into a 1:2 methanol-distilled water mixture with vigorous stirring to form precipitates as a fine white solid. The precipitates thus formed were collected, washed with 5 L of distilled water, and dried in a vacuum oven at 40° C. for 36 hours to prepare 21 g of a soluble polyimide as a white powder.

Workup

  1. dissolutionwas completely dissolved
  2. stirringAfter the resulting mixture was stirred at room temperature for 2 hours
  3. addition3.9 g of NDA was added to the flask
  4. stirringAfter the resulting mixture was stirred at room temperature for 16 hours
  5. distillationa Dean-Stark distillation equipment
  6. temperaturethe reaction solution was refluxed at 140° C. for 3 hours
  7. customthe reaction
  8. customThe reaction solution thus prepared
  9. temperatureto cool to room temperature
  10. customto obtain
  11. customprecipitates
  12. filtrationThe precipitates were filtered
  13. customdried in a vacuum
  14. customdrying oven at 40° C. for one day

Sources & evidence

ORD record
ord-b4622545cc9241188195b7f07dadcbe1
Source dataset
uspto-grants-2007_01
Patent number
US07157204B2

Linked notes

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