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A technology of thiol compounds and aryl sulfides, which is applied in the field of synthesis of oxygen and nitrogen compounds, can solve the problems of high cost, reduce waste liquid, be easy to operate, and improve efficiency
Active Publication Date: 2017-07-21
ZHENGZHOU UNIV
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Problems solved by technology
Although it has been reported that molecular oxygen is used as an oxidant to participate in the oxidation reaction in scientific research work, it has not been applied in actual industrial production, mainly due to the high cost due to the special requirements for the reaction vessel in the high-pressure reaction.
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Embodiment 1
[0028] The preparation method of aryl sulfide compound is as follows:
[0029]
[0030] Add β-naphthol compound (0.5mmol), p-cresylthiol (1.5mmol), sulfonated cobalt phthalocyanine (0.025mmol) in the dry 25mL Schlenk reaction tube, add water 2mL, flush into oxygen, heat to reflux, After reacting for 18 hours, after the reaction, extract with ethyl acetate, dry the extract with anhydrous sodium sulfate, concentrate under reduced pressure to remove the solvent, and separate by column chromatography to obtain the target product.
Embodiment 2
[0032] The preparation method of aryl sulfide compound is as follows:
[0033]
[0034] Add β-naphthol compound (0.5mmol), o-bromothiophenol (83.5mg, 1.5mmol) and copper tetracarboxyphthalocyanine (0.025mmol) to the dry 25mL Schlenk reaction tube, add water 2mL, flush into oxygen, Heat to reflux and react for 24 hours. After the reaction, extract with ethyl acetate, dry the extract with anhydrous sodium sulfate, concentrate under reduced pressure to remove the solvent, and separate by column chromatography to obtain the target product.
Embodiment 3
[0036] The preparation method of aryl sulfide compound is as follows:
[0037]
[0038] Add 6-bromo-2-naphthol compound (0.5mmol), hexanethiol (1.5mmol), sulfonated iron phthalocyanine (0.025mmol) into a dry 25mL Schlenk reaction tube, add 2mL of water, flush into oxygen, and heat Return to reflux and react for 24 hours. After the reaction, extract with ethyl acetate, dry the extract with anhydrous sodium sulfate, concentrate under reduced pressure to remove the solvent, and separate by column chromatography to obtain the target product.
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Abstract
The invention provides a synthetic method for aryl thioether compounds. The synthetic method comprises the following steps: adding phenolic compounds or aminated compounds, thio-alcohol compounds, a transition-metal catalyst and water into a reaction bottle, sealing the reaction bottle, introducing oxygen into the reaction bottle, carrying out heating and a stirring reaction and then successively carrying out extraction, drying, concentration and purifying so as to obtain the aryl thioether compounds. According to the invention, the phthalocyanine transition-metal catalyst is employed for catalysis of the oxidation coupling reaction of phenol or aminated compounds with thio-alcohol compounds so as to prepare the aryl thioether compounds; the synthetic method is simple in steps, easy and practicable in operation and high in product yield, as high as 80% or above and provides a novel approach for synthesis of the aryl thioether compounds; and compared with conventional methods, the method has the advantages that raw materials are cheap and easily available, water is used as a solvent (the catalyst can be dissolved in water), aryl thioether compounds with high separation yield can be obtained under heterogeneous conditions, and reaction efficiency and the atom economy of reaction can be improved.
Description
technical field [0001] The invention relates to the technical field of synthesis of oxygen (sulfur) nitrogen compounds, in particular to a preparation method of aryl sulfide compounds. Background technique [0002] Aryl sulfides are widely found in active compounds in materials science and medicine, and many drugs capable of treating Alzheimer's disease, Parkinson's disease, cancer, malaria, inflammation, and HIV virus have aryl sulfide units in their core structures ( Liu, G.; Huth, J.R.; Olejniczak, E. et al. J. Med. Chem. 2001, 44, 1202-1210.). For example, among thioethers, 2-arylthiophenol compounds have medicinal activity, which can synthesize 4-hydroxy-3-(arylthio)-2H-chromen-2-one, which exhibits antibacterial and analgesic activities. Given the important utility of functionalized aryl sulfides, numerous catalytic reactions have improved C–S bond formation. The general synthesis method is to activate the C-H bond through a catalyst, and an oxidative coupling reacti...
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