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

HRID 224516Notes

Reaction equation

HRID 224516 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:15]1[C:28]2[C:27](=[O:29])[C:26]3[C:21](=[C:22](Cl)[CH:23]=[CH:24][CH:25]=3)[C:20](=[O:31])[C:19]=2[CH:18]=[CH:17][CH:16]=1>CO>[C:2]1([S:1][C:15]2[C:28]3[C:27](=[O:29])[C:26]4[C:21](=[C:22]([S:1][C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)[CH:23]=[CH:24][CH:25]=4)[C:20](=[O:31])[C:19]=3[CH:18]=[CH:17][CH:16]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

The yellow pleochroic 1,5-bis(phenylthio)anthraquinone was prepared as follows: Two equivalents (2.2 g) mercaptobenzene were added to 30 g NN'Dimethylformamide, 5 g potassium carbonate, one equivalent (2.7 g) 1,5-dichloroanthraquinone and heated to reflux for 4 hours, after which 100 ml methanol were added after cooling to 80° C. Upon collecting the crystalline product by filtration, chromatography on alumina using toluene-methanol, and drying, the bright yellow orange crystalline product was obtained.

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 hours
  3. customUpon collecting the crystalline product
  4. filtrationby filtration, chromatography on alumina
  5. customdrying
  6. customthe bright yellow orange crystalline product was obtained

Sources & evidence

ORD record
ord-7b8ff800cdc545d8bbcbe9a696318655
Source dataset
uspto-grants-1980_11
Patent number
US04232949

Reaction notes

Loading…