1,8-Dichloroanthraquinone → HCID 19818010, compound

HRID 1087302Notes

Reaction equation

HRID 1087302 reaction equation
Cl[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3Cl)[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:19]([S:26]([NH2:29])(=[O:28])=[O:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.CO>[CH2:19]([S:26]([NH:29][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[NH:29][S:26]([CH2:19][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)(=[O:28])=[O:27])[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1)(=[O:28])=[O:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 67081,8-DichloroanthraquinoneHCID 7964ChlorobenzeneHCID 11430Potassium CarbonateHCID 78318Benzenemethanesulfonamide

Product 1

HCID 19818010HCID 19818010, compound

Reagents, catalysts & solvents 2

HCID 165397Cupric acetate monohydrateCatalystHCID 887MethanolSolvent

Procedure

A 100ml round bottom flask, equipped with a magnetic stirrer and cooling condenser, was charged with 1,8-dichloroanthraquinone (1.0g), benzylsulfonamide (4.0g), copper acetate monohydrate (1.0g), potassium carbonate (1.4g) and chlorobenzene (20ml). This mixture was refluxed for 2.0 hours and cooled, whereupon methanol (100ml) was added to induce precipitation. The solid was collected, extracted with dichloromethane, treated with charcoal, and recrystallized from a mixture of methanol and dichloromethane to afford a yellow product.

Workup

  1. customA 100ml round bottom flask, equipped with a magnetic stirrer
  2. temperaturecooling condenser
  3. temperatureThis mixture was refluxed for 2.0 hours
  4. additionwas added
  5. customprecipitation
  6. customThe solid was collected
  7. extractionextracted with dichloromethane
  8. additiontreated with charcoal
  9. customrecrystallized from a mixture of methanol and dichloromethane
  10. customto afford a yellow product

Sources & evidence

ORD record
ord-a6edea3114a84d0bb45b5926bee68136
Source dataset
uspto-grants-1991_07
Patent number
US05034547

Reaction notes

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