Acetaminophen → HCID 22749192, compound

HRID 1390348Notes

Reaction equation

HRID 1390348 reaction equation
[Na][Na].[NH2:3][C:4]1[C:17]2[C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:19])[C:8]=2[C:7]([NH2:20])=[C:6]([S:21]([OH:24])(=[O:23])=[O:22])[C:5]=1S(O)(=O)=O.C([NH:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>O.Cl.CN(C)C=O>[NH2:3][C:4]1[C:17]2[C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:19])[C:8]=2[C:7]([NH2:20])=[C:6]([S:21]([OH:24])(=[O:23])=[O:22])[C:5]=1[O:39][C:36]1[CH:37]=[CH:38][C:33]([NH2:32])=[CH:34][CH:35]=1

Participants

8

Reactant 4

HCID 1983AcetaminophenHCID 11430Potassium CarbonateHCID 141233DisodiumHCID 110367402,3-Anthracenedisulfonic acid, 1,4-diamino-9,10-dihydro-9,10-dioxo-

Product 1

HCID 22749192HCID 22749192, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 43 parts of disodium salt of 1,4-diaminoanthraquinone-2,3-disulfonic acid, 30 parts of p-acetylaminophenol, 11 parts of potassium carbonate and 80 parts of dimethylformamide was stirred at 140° C for 3 hours. This reaction solution was poured into 1000 parts of water. The mixture was filtered to remove insoluble components. 300 parts of sodium chloride was added to the filtrate and was filtered again. The cake was washed with 500 parts of a 20% aqueous solution of sodium chloride. The cake thus obtained was dissolved in 450 parts of water and 130 parts of hydrochloric acid was added to the solution. The solution was heated to 95° C and stirred for 10 hours. After cooling the solution was filtered to obtain 1,4-diamino-2-(4'-aminophenoxy)anthraquinone-3-sulfonic acid. 4 parts of sulfanilic acid were added to 200 parts of water and the solution was adjusted to pH 7 with soda ash. 4.1 parts of cyanuric chloride were added to the solution at 0° C, the reaction was continued for 1 hour and after the solution was neutralized, excess cyanuric chloride was removed by filtration. To the filtrate there were added 9 parts of 1,4-diamino-2-(4'-aminophenoxy) anthraquinone-3-sulfonic acid, the solution was kept at 35 - 40° C, a 10% solution of soda ash was added and the reaction was carried out for 2 hours while adjusting the pH to 5 - 7. 60 parts of sodium chloride were added to the reaction solution. The dye precipitated was filtered and dried. There was obtained 13 parts of a dye represented by the following formula: ##STR20## μ max. : 580 mμ in pure water

Workup

  1. filtrationThe mixture was filtered
  2. customto remove insoluble components
  3. addition300 parts of sodium chloride was added to the filtrate
  4. filtrationwas filtered again
  5. washThe cake was washed with 500 parts of a 20% aqueous solution of sodium chloride
  6. customThe cake thus obtained
  7. additionwas added to the solution
  8. temperatureThe solution was heated to 95° C
  9. stirringstirred for 10 hours
  10. temperatureAfter cooling the solution
  11. filtrationwas filtered

Sources & evidence

ORD record
ord-5dc8a387995d4dc8b8c497b258368e1e
Source dataset
uspto-grants-1979_02
Patent number
US04138558

Reaction notes

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