Benzenesulfinic acid, sodium salt → 2-(Phenylsulfonyl-)-naphthacene-5,12-dione

HRID 1196134Notes

Reaction equation

HRID 1196134 reaction equation
F[C:2]1[CH:19]=[CH:18][C:17]2[C:16](=[O:20])[C:15]3[C:6](=[CH:7][C:8]4[C:13]([CH:14]=3)=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:5](=[O:21])[C:4]=2[CH:3]=1.[Na+].[C:23]1([S:29]([O-:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CS(C)=O>[C:23]1([S:29]([C:2]2[CH:19]=[CH:18][C:17]3[C:16](=[O:20])[C:15]4[C:6](=[CH:7][C:8]5[C:13]([CH:14]=4)=[CH:12][CH:11]=[CH:10][CH:9]=5)[C:5](=[O:21])[C:4]=3[CH:3]=2)(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 2723840Benzenesulfinic acid, sodium saltHCID 200898282-Fluorotetracene-5,12-dione

Product 1

HCID 200898352-(Phenylsulfonyl-)-naphthacene-5,12-dione

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1 g (3.62 mmol) of 2-fluoro-naphthacene-5,12-dione, 0.89 g (5.43 mmol) of benzenesulfinic acid sodium salt (sodium benzenesulfinate) and 10 ml of DMSO are stirred at 100° C. for 3 hours. After cooling, the mixture is poured onto water. The crystals are filtered off and dissolved in THF/toluene. The solution is dried over sodium sulfate and evaporated. The residue is recrystallized from THF/toluene/pentane. Yield: 1.35 g (94%), melting point >260° C.

Workup

  1. temperatureAfter cooling
  2. additionthe mixture is poured onto water
  3. filtrationThe crystals are filtered off
  4. dissolutiondissolved in THF/toluene
  5. dry with materialThe solution is dried over sodium sulfate
  6. customevaporated
  7. customThe residue is recrystallized from THF/toluene/pentane

Sources & evidence

ORD record
ord-59cc4d044aa04c63a1d3628bbda9d223
Source dataset
uspto-grants-1992_05
Patent number
US05112977

Reaction notes

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