Dimethyl Sulfoxide → 2-Methylthio-naphthacene-5,12-dione

HRID 275076Notes

Reaction equation

HRID 275076 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.C(=O)([O-])[O-].[K+].[K+].[CH3:28][S:29](C)=O>>[CH3:28][S:29][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

Participants

4

Reactant 3

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 200898282-Fluorotetracene-5,12-dione

Product 1

HCID 200898322-Methylthio-naphthacene-5,12-dione

Procedure

3.62 mmol of 2-fluoro-naphthacene-5,12-dione (prepared according to U.S. Pat. No. 4,522,754), 3.98 mmol of NaSCH3, 10.86 mmol of potassium carbonate and 10 ml of DMSO are stirred at 25° C. for 3 minutes. The mixture is poured onto water. The crystals are filtered off and dissolved in tetrahydrofuran/toluene and the solution is dried over sodium sulfate and evaporated. The residue is recrystallized from THF/toluene/pentane. Yield 1 g (83%); melting point 195°-196° C.

Workup

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

Sources & evidence

ORD record
ord-5c1dae7f86944a478962de2e5a0a4eb9
Source dataset
uspto-grants-1995_02
Patent number
US05391749

Reaction notes

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