Acetic Anhydride → HCID 22076399, compound

HRID 1376753Notes

Reaction equation

HRID 1376753 reaction equation
[NH:1]([C:8]1[CH:9]=[C:10]([C:24]([OH:26])=[O:25])[C:11](=[CH:15][C:16]=1[NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]([OH:14])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(=O)C)(=O)C>C1(C)C=CC=CC=1>[NH:17]([C:16]1[CH:15]=[C:11]2[C:12](=[O:14])[O:26][C:24](=[O:25])[C:10]2=[CH:9][C:8]=1[NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 22918353HCID 22918353, compound

Product 1

HCID 22076399HCID 22076399, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A steady stream of argon is passed through a suspension of 23.4 g (67.18 mmol) of 4,5-bis(anilino)phthalic acid in 250 ml of toluene, and 19.0 m1(201.5 mmol, 3 eq) of acetic anhydride is added. The reaction mixture is heated to 60°-65° for 90 minutes with vigorous stirring. The reaction mixture is cooled to 10° for 30 minutes, and the yellow to orange crystals are filtered off and washed with toluene/hexane to yield the title compound in the form of yellow crystals, FAB-MS: 331 [M+ +H].

Workup

  1. additionis added
  2. temperatureThe reaction mixture is heated to 60°-65° for 90 minutes with vigorous stirring
  3. temperatureThe reaction mixture is cooled to 10° for 30 minutes
  4. filtrationthe yellow to orange crystals are filtered off
  5. washwashed with toluene/hexane

Sources & evidence

ORD record
ord-af606a296c224146994f3841faf6b2d6
Source dataset
uspto-grants-1997_09
Patent number
US05663336

Reaction notes

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