Hydrogen Peroxide → HCID 66915141, compound

HRID 2059541Notes

Reaction equation

HRID 2059541 reaction equation
[C:1]1([S:7][C:8]2[CH:21]=[CH:20][C:19]3[S:18][C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:11](=[O:22])[C:10]=3[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(#N)C.S(=O)(=O)(O)[OH:27].OO>O>[C:1]1([S:7]([C:8]2[CH:21]=[CH:20][C:19]3[S:18][C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:11](=[O:22])[C:10]=3[CH:9]=2)=[O:27])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 669152892-(Phenylthio)thioxanthone

Product 1

HCID 66915141HCID 66915141, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

While 11.2 parts of 2-(phenylthio)thioxanthone synthesized in Production Example 1, 215 parts of acetonitrile, and 0.02 parts of sulfuric acid were stirred at 40° C., 4.0 parts of a 30% aqueous hydrogen peroxide solution was dropped thereto slowly and then a reaction was performed at 40 to 45° C. for 14 hours. Subsequently, the reaction solution was cooled to room temperature (about 25° C.) and then was poured into 200 parts of distilled water, so that the product was precipitated. This was filtered and the residue was washed with water until the pH of the filtrate became neutral. Then the residue was dried under reduced pressure, affording a yellow powdery product. The product was purified by column chromatography (eluate: ethyl acetate/toluene=⅓:volume ratio) to afford 2-[(phenyl)sulfinyl]thioxanthone in a yield of 83%. The product was identified by 1H-NMR {d6-dimethyl sulfoxide, δ (ppm) 8.75 (1H, s), 8.45 (1H, d), 8.01 (2H, d), 7.75-7.85 (4H, m), 7.53-7.62 (4H, m)}.

Workup

  1. temperatureSubsequently, the reaction solution was cooled to room temperature (about 25° C.)
  2. customwas precipitated
  3. filtrationThis was filtered
  4. washthe residue was washed with water until the pH of the filtrate
  5. customThen the residue was dried under reduced pressure
  6. customaffording a yellow powdery product
  7. customThe product was purified by column chromatography (eluate: ethyl acetate/toluene=⅓:volume ratio)

Sources & evidence

ORD record
ord-71b842c4d18a48378a2c92fdef1c20f5
Source dataset
uspto-grants-2012_10
Patent number
US08278030B2

Reaction notes

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