Acetic Acid → HCID 22287028, compound

HRID 412733Notes

Reaction equation

HRID 412733 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[C:9]1([C:15]23[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[C:21]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:20]2([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)C(=O)OC3=O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:44]([OH:47])(=O)[CH3:45]>>[C:25]1([C:22]2[C:21]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)=[C:20]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:15]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:24]3[C:45]=2[C:44](=[O:47])[N:7]2[C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=4[N:8]=[C:23]23)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 7243O-PhenylenediamineHCID 54556085HCID 54556085, compound

Product 1

HCID 22287028HCID 22287028, compound

Procedure

A 500 ml round-bottom flask equipped with a stirrer and reflux condenser is charged with 8.34 9 (73.3 mmol) of o-phenylenediamine (95%), 33.0 g (66.3 mmol) of 1,2,3,4-tetraphenyl-phthalic anhydride, and 200 ml of glacial acetic acid. Under nitrogen atmosphere, the mixture is stirred and heated at reflux for 11 hours. The slurry is cooled and the yellow solid is isolated by filtration. The solid is washed with water and then with methanol. 35.1 g of an yellow solid is obtained (92%).

Workup

  1. customA 500 ml round-bottom flask equipped with a stirrer
  2. temperaturereflux condenser
  3. temperatureheated
  4. temperatureat reflux for 11 hours
  5. temperatureThe slurry is cooled
  6. customthe yellow solid is isolated by filtration
  7. washThe solid is washed with water

Sources & evidence

ORD record
ord-520f4faf814f4d4abe7f0d289253f82e
Source dataset
uspto-grants-2003_05
Patent number
US06562981B2

Reaction notes

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