1,5-Dichloroanthraquinone → 1-n-Octylsulfonylamino-5-chloroanthraquinone

HRID 1087303

Reaction equation

HRID 1087303 reaction equation
Cl[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([Cl:17])[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][S:27]([NH2:30])(=[O:29])=[O:28].C(=O)([O-])[O-].[K+].[K+]>ClC1C=CC=CC=1>[CH2:26]([S:27]([NH:30][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([Cl:17])[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1)(=[O:28])=[O:29])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH3:19]

Participants

5

Reactant 3

HCID 67111,5-DichloroanthraquinoneHCID 11430Potassium CarbonateHCID 2295971-Octanesulfonamide

Product 1

HCID 198180091-n-Octylsulfonylamino-5-chloroanthraquinone

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

1,5-dichloroanthraquinone (1.0g), n-octanesulfonamide (0.77g), potassium carbonate (1.0g), cupric acetate monohydrate (1.0g) and chlorobenzene (15ml) were refluxed for 4 hours. The solvent was evaporated at reduced pressure and the residue was extracted with toluene. After filtration the extract was separated by chromatography on silica using toluene as eluent to give the desired product as the second fraction.

Workup

  1. customThe solvent was evaporated at reduced pressure
  2. extractionthe residue was extracted with toluene
  3. filtrationAfter filtration the extract
  4. customwas separated by chromatography on silica

Sources & evidence

ORD record
ord-7bd1e0d106704655b73d1ab25b925ab7
Source dataset
uspto-grants-1991_07
Patent number
US05034547

Linked notes

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