Dimethylformamide → 2-(Phenylthio)thioxanthone

HRID 1916018Notes

Reaction equation

HRID 1916018 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

Uniformly mixed were 11.0 parts of 2-chlorothioxanthone, 4.9 parts of thiophenol, 2.5 parts of potassium hydroxide, 162 parts of N,N-dimethylformamide, and allowed to react at 130° C. for 9 hours. Subsequently, the reaction solution was cooled to room temperature (about 25° C.) and poured into 200 parts of distilled water, so that the product was precipitated. The product was filtered, and the residue was washed with water until the pH of the filtrate became neutral. Subsequently, the residue was dried under reduced pressure, so that a yellow powdery product was obtained. The product was purified by column chromatography (eluent: toluene/hexane=1/1 in volume ratio) to give 2-(phenylthio)thioxanthone in a yield of 45%. The product was identified by 1H-NMR {d6-dimethylsulfoxide, 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. additionUniformly mixed
  2. customto react at 130° C. for 9 hours
  3. customwas precipitated
  4. filtrationThe product was filtered
  5. washthe residue was washed with water until the pH of the filtrate
  6. customSubsequently, the residue was dried under reduced pressure, so that a yellow powdery product
  7. customwas obtained
  8. customThe product was purified by column chromatography (eluent: toluene/hexane=1/1 in volume ratio)

Sources & evidence

ORD record
ord-a07c100ca8ee4a0886c85189012e1b13
Source dataset
uspto-grants-2013_12
Patent number
US08617787B2

Reaction notes

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