Methyl Benzoate → Vat Blue 4

HRID 1741199Notes

Reaction equation

HRID 1741199 reaction equation
[NH2:1][C:2]1(Br)[CH:15]=[C:14](Br)[C:13]2[C:12](=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:18])[C:4]=2[CH2:3]1.O([C:27]1[CH:33]=[CH:32][C:30]([NH2:31])=[CH:29][CH:28]=1)C1C=CC=CC=1.[C:34]([O:42]C)(=O)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[C:44]([O-])(=[O:46])C.[K+]>>[CH:9]1[CH:10]=[C:11]2[C:12]([C:13]3[CH:14]=[CH:15][C:2]4[NH:1][C:29]5[C:28]6[C:44]([C:36]7[C:35]([C:34](=[O:42])[C:27]=6[CH:33]=[CH:32][C:30]=5[NH:31][C:3]=4[C:4]=3[C:5](=[O:18])[C:6]2=[CH:7][CH:8]=1)=[CH:40][CH:39]=[CH:38][CH:37]=7)=[O:46])=[O:17]

Participants

5

Reactant 4

HCID 7150Methyl Benzoate2×HCID 8764(4-Aminophenoxy)benzeneHCID 517044Potassium Acetate2×HCID 21195064HCID 21195064, compound

Product 1

HCID 6690Vat Blue 4

Conditions

Temperature
137.5 °C

Procedure

A black indanthrone compound was prepared by adding 114.4 parts 2-amino-2,4-dibromoanthraquinone and 57.4 parts 4-phenoxyaniline in 875 parts methyl benzoate to 58.8 parts potassium acetate and 3 parts cupric acetate. This mixture was then heated with stirring to 135-140 degrees C. for 7 hours at which time another 220 parts methyl benzoate was added. Stirring at 135-140 degrees C. continued for an additional 6 hours. The mixture was cooled to room temperature and 58.8 parts potassium acetate was added. The mixture was then heated to reflux using a Dean-Stark trap to remove low boiling by products which permitted the temperature in the flask to remain at 196-198 degrees C. The mixture was stirred at reflux for 1.5 hours and cooled with stirring. The product was isolated as in Example 2 and gave a similar yield of a black dye composition consisting mainly of 8,17-bis(4-phenoxyphenylamino)indanthrone.

Workup

  1. temperatureThis mixture was then heated
  2. stirringStirring at 135-140 degrees C
  3. temperatureThe mixture was cooled to room temperature
  4. temperatureThe mixture was then heated
  5. temperatureto reflux
  6. customto remove low boiling by products which
  7. customto remain at 196-198 degrees C
  8. stirringThe mixture was stirred
  9. temperatureat reflux for 1.5 hours
  10. temperaturecooled
  11. stirringwith stirring
  12. customThe product was isolated as in Example 2
  13. customgave a similar yield of a black dye composition

Sources & evidence

ORD record
ord-a4070c47fbbf4e948e0f8da68c9de219
Source dataset
uspto-grants-1999_10
Patent number
US05973038

Reaction notes

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