1-Chloroanthraquinone → 1-(n-Octylsulfonylamino)anthraquinone

HRID 1087301

Reaction equation

HRID 1087301 reaction equation
Cl[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:18]([S:26]([NH2:29])(=[O:28])=[O:27])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.ClC1C=CC=CC=1Cl>[CH2:18]([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][CH:12]=3)[C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1)(=[O:27])=[O:28])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 3

HCID 67091-ChloroanthraquinoneHCID 11430Potassium CarbonateHCID 2295971-Octanesulfonamide

Product 1

HCID 199903611-(n-Octylsulfonylamino)anthraquinone

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 72391,2-DichlorobenzeneSolvent

Procedure

A 100ml round bottom flask, equipped with a magnetic stirrer and cooling condenser, was charged with 1-chloroanthraquinone (2.0g), n-octylsulfonamide (3.0g), copper acetate (0.8g), potassium carbonate (0.8g) and o-dichlorobenzene (25ml). This mixture was slowly heated to reflux. After 2.5 hours the reaction mixture was cooled and filtered. Methanol was then added to induce precipitation, and after filtration the solid was recrystallized from a mixture of dichloromethane and methanol to give a yellow product.

Workup

  1. customA 100ml round bottom flask, equipped with a magnetic stirrer
  2. temperaturecooling condenser
  3. temperatureThis mixture was slowly heated to reflux
  4. temperatureAfter 2.5 hours the reaction mixture was cooled
  5. filtrationfiltered
  6. additionMethanol was then added
  7. customprecipitation
  8. filtrationafter filtration the solid
  9. customwas recrystallized from a mixture of dichloromethane and methanol
  10. customto give a yellow product

Sources & evidence

ORD record
ord-3e6a13242a364f83931fe3aa4a4de4e3
Source dataset
uspto-grants-1991_07
Patent number
US05034547

Linked notes

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