Dimethylformamide → 2-(Phenylthio)thioxanthone

HRID 2059540Notes

Reaction equation

HRID 2059540 reaction equation
Cl[C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:16])[C:4]=2[CH:3]=1.[C:17]1([SH:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[OH-].[K+].CN(C)C=O>O>[C:17]1([S:23][C:2]2[CH:15]=[CH:14][C:13]3[S:12][C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:5](=[O:16])[C:4]=3[CH:3]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7969ThiophenolHCID 14797Potassium HydroxideHCID 6188482-Chlorothioxanthone

Product 1

HCID 669152892-(Phenylthio)thioxanthoneYield 45%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

After mixing 11.0 parts of 2-chlorothioxanthone, 4.9 parts of thiophenol, 2.5 parts of potassium hydroxide, and 162 parts of N,N-dimethylformamide uniformly and then making them react at 130° C. for 9 hours, 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:toluene/hexane=1/1:volume ratio) to afford 2-(phenylthio)thioxanthone in a yield of 45%. The product was identified by 1H-NMR {d6-dimethyl sulfoxide, δ (ppm) 8.43 (1H, d), 8.25 (1H, s), 7.75-7.90 (3H, m), 7.66 (1H, d), 7.60 (1H, t), 7.42-7.46 (5H, m)}.

Workup

  1. customreact at 130° C. for 9 hours
  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:toluene/hexane=1/1:volume ratio)

Sources & evidence

ORD record
ord-e66bf91e69b745bdbc7454a4a16ceb67
Source dataset
uspto-grants-2012_10
Patent number
US08278030B2

Reaction notes

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