Reaction #2146722

Reaction equation

2-chlorothioxanthone

thiophenol

potassium hydroxide

N,N-dimethylformamide

→

2-(phenylthio)thioxanthone

Yield 45.0%

Solvents

water

Conditions

Workup

1. 1
   Otherreact at 130° C. for 9 hours
2. 2
   Otherwas precipitated
3. 3
   FiltrationThis was filtered
4. 4
   Washthe residue was washed with water until the pH of the filtrate
5. 5
   OtherThen the residue was dried under reduced pressure
6. 6
   Otheraffording a yellow powdery product
7. 7
   OtherThe product was purified by column chromatography (eluate:toluene/hexane=1/1:volume ratio)

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)}.

Source