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Synthetic method of medical intermediate carbonyl-replacement aryl thioether compound

A synthesis method and technology of aryl sulfide, which is applied in the synthesis of sulfide compounds and the synthesis of carbonyl-substituted aryl sulfide compounds, can solve the problems of low reaction yield and reaction process to be optimized, and achieve broad market prospects, The effect of mild reaction process

Inactive Publication Date: 2016-03-02
张道敬
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] As mentioned above, the prior art discloses a variety of synthesis methods for thioether compounds. However, these methods still cannot meet the general needs in the fields of chemical and pharmaceutical synthesis, and there are still many defects such as low reaction yield and reaction process to be optimized.

Method used

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  • Synthetic method of medical intermediate carbonyl-replacement aryl thioether compound
  • Synthetic method of medical intermediate carbonyl-replacement aryl thioether compound
  • Synthetic method of medical intermediate carbonyl-replacement aryl thioether compound

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Effect test

Embodiment 1

[0043]

[0044] At room temperature and under a nitrogen atmosphere, to an appropriate amount of organic solvent (a mixture of chlorobenzene and DMSO with a volume ratio of 1:2), add 100mmol of the compound of the above formula (I), 140mmol of the compound of the above formula (II), and 10mmol of the catalyst (8mmolCu( PPh 3 ) 2 NO 3 With 2mmolNi(acac) 2 The mixture), 5mmol of organic ligand L1, 10mmol of activator p-methoxyphenyl tellurium oxide and 200mmol of basic cesium carbonate, then heated to 60°C, and stirred at this temperature for 8 hours;

[0045] After the reaction is completed, the reaction system is naturally cooled to room temperature, filtered, and 5% by mass hydrochloric acid aqueous solution is added to the filtrate, shaken thoroughly, and then ethyl acetate is added for extraction 2-3 times, and the organic phases are combined and decompressed. After distillation, the residue was subjected to 300-400 mesh silica gel column chromatography, and washed with acetone...

Embodiment 2

[0048]

[0049] Under room temperature and nitrogen atmosphere, to an appropriate amount of organic solvent (a mixture of chlorobenzene and DMSO with a volume ratio of 1:2), add 100mmol of the compound of the above formula (I), 170mmol of the compound of the above formula (II), and 12mmol of catalyst (8mmolCu( PPh 3 ) 2 NO 3 With 4mmolNi(acac) 2 ), 8mmol of organic ligand L1, 15mmol of activator p-methoxyphenyl tellurium oxide and 250mmol of basic cesium carbonate, then the temperature is raised to 75°C, and the reaction is stirred at this temperature for 6 hours;

[0050] After the reaction is completed, the reaction system is naturally cooled to room temperature, filtered, the filtrate is added to the filtrate with a 7% mass percent hydrochloric acid aqueous solution, fully shaken, and then ethyl acetate is added for extraction 2-3 times, and the organic phases are combined and decompressed After distillation, the residue was subjected to silica gel column chromatography of 300-...

Embodiment 3

[0053]

[0054] At room temperature and under a nitrogen atmosphere, to an appropriate amount of organic solvent (a mixture of chlorobenzene and DMSO with a volume ratio of 1:2), 100mmol of the compound of the above formula (I), 200mmol of the compound of the above formula (II), and 16mmol of the catalyst (12mmolCu( PPh 3 ) 2 NO 3 With 4mmolNi(acac) 2 ), 10mmol of organic ligand L1, 20mmol of activator p-methoxyphenyl tellurium oxide and 300mmol of basic cesium carbonate, then the temperature is raised to 90°C, and the reaction is stirred at this temperature for 5 hours;

[0055] After the reaction is completed, the reaction system is naturally cooled to room temperature, filtered, and a 10% aqueous hydrochloric acid solution is added to the filtrate, shaken thoroughly, and then ethyl acetate is added for extraction 2-3 times, and the organic phases are combined and decompressed After distillation, the residue was subjected to silica gel column chromatography of 300-400 mesh, and ...

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Abstract

The invention relates to a synthetic method of a carbonyl-replacement aryl thioether compound as shown in the formula (III). The method comprises the steps of making a compound in the formula (I) react with a compound in the formula (II) under the nitrogen atmosphere in organic solvent with the existence of a catalyst, organic ligand, an activating agent and alkali, conducting after-treatment after the reaction is ended, obtaining the compound as shown in the formula (III), wherein each R1 is independent C1-C6 alkyl; R2 is C1-C6 alkyl, C1-C6 alkoxy, halogen or nitryl; X is halogen. In conclusion, according to the synthetic method of the carbonyl-replacement aryl thioether compound, a novel composite reaction system is adopted, a target product high in yield can be obtained through comprehensive selection of the catalyst, the organic ligand, the activating agent and the alkali, the reaction process is mild, requirements of such fields as chemical engineering and medicine are satisfied, and the market prospect is broad.

Description

Technical field [0001] The invention relates to a method for synthesizing a sulfide compound, in particular to a method for synthesizing a carbonyl substituted aryl sulfide compound that can be used as a pharmaceutical intermediate, and belongs to the field of organic chemistry, especially the synthesis of pharmaceutical intermediates. Background technique [0002] In the field of organic chemistry, especially medicinal chemistry, sulfide is a very important sulfur-containing compound. Because of its potential biological activity, it has attracted much attention in the fields of organic synthesis and drug synthesis. Among them, carbonyl substituted thioethers are commonly used intermediates in the synthesis of heterocyclic compounds, and they are widely used in pharmaceutical compounds. Therefore, the development of new synthetic methods for carbonyl substituted thioethers has been the research interest of many researchers. [0003] In recent years, some synthesis processes of carb...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/14C07C323/22
CPCB01J31/2404B01J2231/4294B01J2531/0213B01J2531/0238B01J2531/16B01J2531/847C07B45/06C07C319/14C07C319/28C07C323/22
Inventor 张妍
Owner 张道敬
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