1,5-Dichloroanthraquinone → 9,10-Anthracenedione, 1,5-bis(phenylthio)-

HRID 1995500Notes

Reaction equation

HRID 1995500 reaction equation
Cl[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9](Cl)[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:19]1([SH:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:19]1([S:25][C:2]2[C:15]3[C:14](=[O:16])[C:13]4[C:8](=[C:9]([S:25][C:19]5[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=5)[CH:10]=[CH:11][CH:12]=4)[C:7](=[O:18])[C:6]=3[CH:5]=[CH:4][CH:3]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 67111,5-DichloroanthraquinoneHCID 7969ThiophenolHCID 11430Potassium Carbonate

Product 1

HCID 919149,10-Anthracenedione, 1,5-bis(phenylthio)-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

1,5-Dichloroanthraquinone (100 parts) is added at room temperature with stirring to a mixture of dimethylformamide (474 parts), thiophenol (135 parts) and potassium carbonate (63 parts). The suspension is heated at 125° C. for 3 hours, cooled to room temperature and then cooled to 5° C. for 1 hour. The precipitate is filtered off and washed with a 50/50 mixture of 95% ethanol and 8% sodium hydroxide solution (2×250 parts). The filter cake is then slurried with a further 500 parts of the ethanol/sodium hydroxide solution mixture. After stirring at room temperature for 1 hour, the precipitate is filtered off and washed again with ethanol/sodium hydroxide solution mixture (5×100 parts), followed by water (250 parts) containing glacial acetic acetic acid (25 parts) and finally water (3×250 parts). The filter-cake is dried at 70° C. giving 140.4 parts of 1,5-bis(phenylthio) anthraquinone, mp (melting point) 256° C.

Workup

  1. temperaturecooled to room temperature
  2. temperaturecooled to 5° C. for 1 hour
  3. filtrationThe precipitate is filtered off
  4. washwashed with a 50/50 mixture of 95% ethanol and 8% sodium hydroxide solution (2×250 parts)
  5. filtrationthe precipitate is filtered off
  6. washwashed again with ethanol/sodium hydroxide solution mixture (5×100 parts)
  7. additioncontaining glacial acetic acetic acid (25 parts) and finally water (3×250 parts)
  8. customThe filter-cake is dried at 70° C.

Sources & evidence

ORD record
ord-6575dbc5dcde482b85ae7aee208b8732
Source dataset
uspto-grants-1983_09
Patent number
US04405211

Reaction notes

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