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Method for catalytically synthesizing diaryl thioether through phenylthiourea in aqueous phase under microwave radiation

A diaryl sulfide and microwave radiation technology, which is applied in the preparation of sulfide, organic chemistry, etc., can solve the problems of reduced reaction yield, high catalyst/ligand loading, high cost, etc., and achieve simple operation, high yield, The effect of less by-products

Active Publication Date: 2018-04-24
FUJIAN MEDICAL UNIV
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  • Application Information

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Problems solved by technology

The above methods all use organic solvents to varying degrees, and there are also disadvantages of high catalyst / ligand loading, relatively high cost, and often lower reaction yields due to the occurrence of side reactions.
[0004] The preparation of diaryl sulfides by catalyzing phenylthioureas and substituted iodobenzenes in pure aqueous systems has rarely been reported so far

Method used

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  • Method for catalytically synthesizing diaryl thioether through phenylthiourea in aqueous phase under microwave radiation
  • Method for catalytically synthesizing diaryl thioether through phenylthiourea in aqueous phase under microwave radiation
  • Method for catalytically synthesizing diaryl thioether through phenylthiourea in aqueous phase under microwave radiation

Examples

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Embodiment 1

[0028] Example 1: 4-methyldiphenyl sulfide: 1.0 mmol of phenylthiourea, 1.2 mmol of 4-methyl iodobenzene, NiCl 2 5 mol-%, 1,10-phenanthroline 10 mol-%, Al powder 200 mol-%, water 3.0 mL, stirred for 5 min. Placed in a microwave reactor and heated to 100 °C under 150 W power for continuous reaction for 40 min. After the reaction was completed, it was cooled to room temperature, and the product was extracted with ethyl acetate, washed with saturated Na 2 SO 4 Dry and concentrate under reduced pressure, and the product is purified by column chromatography to obtain a colorless liquid with a yield of 86%.

Embodiment 2

[0029] Example 2: 5-methyldiphenyl sulfide: the preparation method is the same as in Example 1, and 1.2 mmol of 3-methyliodobenzene is added to the reaction vessel to obtain a colorless liquid with a yield of 83%.

Embodiment 3

[0030] Example 3: 6-methyldiphenyl sulfide: the preparation method is the same as that of Example 1, adding 1.2 mmol of 2-methyl iodobenzene into the reaction vessel to obtain a colorless liquid with a yield of 69%.

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Abstract

The invention discloses a method for catalytically synthesizing diaryl thioether through phenylthiourea in aqueous phase under microwave radiation. The method includes: in an aqueous phase condition,adopting substituted phenylthiourea and substituted iodobenzene as raw materials; introducing microwaves as an assistant synthesis means; quickly preparing diaryl thioether compound through efficientcatalysis. Compared with the prior art, the method has the advantages that reaction speed is obviously increased when compared with conventional heating, and the method is suitable for a lot of functional groups, safe, efficient, low in cost, high in yield, few in byproduct, mild in condition, simple to operate and environment-friendly.

Description

technical field [0001] The invention relates to a method for preparing diaryl sulfide by catalyzing phenylthiourea and iodobenzene in water phase under microwave radiation. Background technique [0002] Diaryl sulfide compound is a valuable intermediate of medicine, pesticide and dye, and has very important industrial application value. For example, it is widely used in the fields of biology, medicine, pesticides, dye intermediates and organic synthesis. It is used as an α-phenylthiolating agent for carbonyl compounds, reducing aromatic sulfonic acids to mercaptans, and reacting with aromatic halides to form hydrocarbon sulfides. It is 1 , Catalyst for cis and trans isomerization reactions of 2-stilbene, stereoselective cyclization reactions of epoxy silane alcohol ethers. Diphenyl disulfide is a commonly used reagent for introducing phenylthio functional groups into molecules, which can react with many organic nucleophiles and free radicals; it can also generate phenylthio...

Claims

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Application Information

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IPC IPC(8): C07C321/30C07C319/14C07C323/09C07C323/20
CPCC07C319/14C07C321/30C07C323/09C07C323/20
Inventor 林晨柯方许建华施孙洁黄凌凌涂书清
Owner FUJIAN MEDICAL UNIV
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