Nitrobenzene → 1-n-Octylsulfonylamino-8-(1'-ethylhexanoylamino)anthraquinone

HRID 1087305Notes

Reaction equation

HRID 1087305 reaction equation
[CH2:1]([S:9]([NH:12][C:13]1[C:26]2[C:25](=[O:27])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][C:23]=3[NH2:28])[C:18](=[O:29])[C:17]=2[CH:16]=[CH:15][CH:14]=1)(=[O:11])=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:30]([C:32](=[O:39])[CH:33](Cl)[CH2:34][CH2:35][CH2:36][CH3:37])[CH3:31].[N+](C1C=CC=CC=1)([O-])=O>CO>[CH2:1]([S:9]([NH:12][C:13]1[C:26]2[C:25](=[O:27])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][C:23]=3[NH:28][CH:33]([CH2:34][CH2:35][CH2:36][CH3:37])[C:32]([CH2:30][CH3:31])=[O:39])[C:18](=[O:29])[C:17]=2[CH:16]=[CH:15][CH:14]=1)(=[O:10])=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 7416NitrobenzeneHCID 126422284-Chlorooctan-3-oneHCID 198180061-(n-Octylsulfonylamino)-8-aminoanthraquinone

Product 1

HCID 1317169531-n-Octylsulfonylamino-8-(1'-ethylhexanoylamino)anthraquinone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(n-octylsulfonylamino)-8-aminoanthraquinone (0.25g), 1-ethylhexanoyl chloride (0.5g) and nitrobenzene (5ml) were heated at reflux for 10 mins. After addition of methanol (10ml), the mixture was heated on a steam bath for a further 10 mins to destroy excess acid chloride. 0n evaporation of low-boiling material, the remaining liquid was diluted with toluene (100ml) and separated by chromatography on a silica gel column. Nitrobenzene eluted first, and the material eluted with a 50:50 mixture of toluene:ethyl acetate was collected. The solvent was evaporated and ethanol was added to the residue, which upon trituration afforded the product as a yellow solid.

Workup

  1. temperatureat reflux for 10 mins
  2. temperaturethe mixture was heated on a steam bath for a further 10 mins
  3. customto destroy excess acid chloride
  4. custom0n evaporation of low-boiling material
  5. additionthe remaining liquid was diluted with toluene (100ml)
  6. customseparated by chromatography on a silica gel column
  7. washNitrobenzene eluted first
  8. washthe material eluted with a 50:50 mixture of toluene
  9. customethyl acetate was collected
  10. customThe solvent was evaporated
  11. additionethanol was added to the residue, which upon trituration

Sources & evidence

ORD record
ord-8197cbd2d89e4ecabeead3476c579b88
Source dataset
uspto-grants-1991_07
Patent number
US05034547

Reaction notes

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