Potassium Carbonate → 1-(n-Octylsulfonylamino)-8-aminoanthraquinone

HRID 1087304

Reaction equation

HRID 1087304 reaction equation
[NH2:1][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.[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:12]1[C:13]2[C:14](=[O:16])[C:15]3[C:6](=[CH:5][CH:4]=[CH:3][C:2]=3[NH2:1])[C:7](=[O:18])[C:8]=2[CH:9]=[CH:10][CH:11]=1)(=[O:29])=[O:28])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH3:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2236691-Amino-8-chloroanthraquinoneHCID 2295971-Octanesulfonamide

Product 1

HCID 198180061-(n-Octylsulfonylamino)-8-aminoanthraquinone

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

1-(n-octylsulfonylamino)-8-aminoanthraquinone was prepared as follows. 1-amino-8-chloroanthraquinone (1.0g), n-octanesulfonamide (1.0g), potassium carbonate (1.0g), cupric acetate monohydrate (0.85g) and chlorobenzene (16.0g) were refluxed for 5.5 hours. The cooled mixture was filtered and aqueous methanol was added to the filtrate. The supernatant liquid was decanted and the remaining oil was dissolved in dichloromethane. On addition of methanol and partial evaporation of the solvent, the product separated as a red solid.

Workup

  1. filtrationThe cooled mixture was filtered
  2. additionaqueous methanol was added to the filtrate
  3. customThe supernatant liquid was decanted
  4. dissolutionthe remaining oil was dissolved in dichloromethane
  5. additionOn addition of methanol and partial evaporation of the solvent
  6. customthe product separated as a red solid

Sources & evidence

ORD record
ord-83651583e42e4f30a2ee99efb5716dee
Source dataset
uspto-grants-1991_07
Patent number
US05034547

Linked notes

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