Anthranilic Acid → 4H-3,1-Benzoxazin-4-one, 2,2'-(1,4-phenylene)bis-

HRID 1835906Notes

Reaction equation

HRID 1835906 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[OH-:11].[Na+].[C:13](Cl)(=[O:23])[C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=O)=[CH:16][CH:15]=1.O>C(C(C)=O)C(C)C>[C:14]1([C:13]2[O:23][C:1](=[O:11])[C:2]3[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=3[N:4]=2)[CH:22]=[CH:21][C:17]([C:18]2[O:9][C:1](=[O:10])[C:2]3[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=3[N:4]=2)=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 227Anthranilic AcidHCID 962WaterHCID 7488Terephthaloyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 30984224H-3,1-Benzoxazin-4-one, 2,2'-(1,4-phenylene)bis-

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent2×

Procedure

Anthranilic acid (1 part by weight) and 0.35 parts of NaOH were dissolved in approximately 5.5 parts of methyl isobutyl ketone (MIBK). With stirring, a solution of 0.7 parts of terephthaloyl dichloride in 3 parts of MIBK was slowly added at approximately 60 to 70° C. to the mixture. After the addition, the mixture was reacted at 60 to 70° C. for 2 hours. Water was distilled off and approximately 2 parts of acetic anhydride was added. The mixture was then reacted for 7 hours at reflux conditions. Water was then added, the batch was refluxed for 0.5 hours and then the MIBK was distilled off. Approximately 1 part of 50% NaOH solution was then added and the reaction mixture was cooled, filtered and dried to give 2,2′-p-phenylenebis(3,1-benzoxazin-4-one).

Workup

  1. additionAfter the addition
  2. customthe mixture was reacted at 60 to 70° C. for 2 hours
  3. distillationWater was distilled off
  4. additionapproximately 2 parts of acetic anhydride was added
  5. customThe mixture was then reacted for 7 hours
  6. temperatureat reflux conditions
  7. temperaturethe batch was refluxed for 0.5 hours
  8. distillationthe MIBK was distilled off
  9. additionApproximately 1 part of 50% NaOH solution was then added
  10. temperaturethe reaction mixture was cooled
  11. filtrationfiltered
  12. customdried

Sources & evidence

ORD record
ord-54b81908d92043a893de12736be9ec0a
Source dataset
uspto-grants-2004_08
Patent number
US06774232B2

Reaction notes

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