Anthranilic Acid → Benzoic acid, 2,2'-[1,4-phenylenebis(carbonylimino)]bis-

HRID 2254015Notes

Reaction equation

HRID 2254015 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[C:11](=[O:14])([O-])[O-:12].[Na+].[Na+].[C:17](Cl)(=[O:27])[C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1.Cl>O.CC(C)=O>[C:17]([NH:4][C:3]1[C:2](=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:11]([OH:12])=[O:14])(=[O:27])[C:18]1[CH:26]=[CH:25][C:21]([C:22]([NH:4][C:3]2[C:2](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:1]([OH:10])=[O:9])=[O:23])=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 227Anthranilic AcidHCID 313Hydrochloric AcidHCID 7488Terephthaloyl chlorideHCID 10340Sodium Carbonate

Product 1

HCID 1069143Benzoic acid, 2,2'-[1,4-phenylenebis(carbonylimino)]bis-

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

Anthranilic acid (14.0 parts) and 11.7 parts of sodium carbonate were dissolved in 250 parts of water, and a solution obtained by dissolving 10.1 parts of terephthalic acid dichloride in 60 parts of acetone was added dropwise to the above solution with stirring at 20 to 30° C. Reaction was carried out at room temperature for 2 hours after the dropwise addition and further under acetone reflux for one hour. Then, concentrated hydrochloric acid was added to make the reaction system acidic, and the precipitate was filtered and dried to obtain 19.1 parts of terephthaloyl-bisanthranilic acid.

Workup

  1. customa solution obtained
  2. additionwas added dropwise to the above solution
  3. customReaction
  4. additionafter the dropwise addition
  5. filtrationthe precipitate was filtered
  6. customdried

Sources & evidence

ORD record
ord-97d1d89f7b0744529c893e517b63485f
Source dataset
uspto-grants-1993_08
Patent number
US05234681

Reaction notes

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