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Preparation method of thioether compound

A technology of thioether compound and reaction, which is applied in the field of preparation of thioether compound, can solve the problems of being unfriendly to the human body or the environment, complicated reaction process, and many side reactions, and achieves favorable promotion and application, simple reaction process, and avoiding side effects. The effect of the reaction

Inactive Publication Date: 2019-08-02
GUANGDONG UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, more thioether compounds are prepared by cross dehydrogenation coupling (CDC) reaction, but in the current preparation process, most of the solvents used are organic solvents with certain toxicity, which are not friendly to human body or environment. Complicated, requiring the use of catalysts or ligands, resulting in higher costs and more side reactions, leaving a large room for improvement

Method used

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  • Preparation method of thioether compound
  • Preparation method of thioether compound
  • Preparation method of thioether compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Example 1 Synthesis of 9-((4-methylphenyl)thio)-9H-oxanthene

[0051] The structure of 9-((4-methylphenyl)thio)-9H-xanthene is shown below:

[0052]

[0053]The specific preparation process is: put 49.6mg of p-methylthiophenol (0.4mmol) and 36.4mg of xanthene (0.2mmol) into 15mL Schlenk, add 2mL of absolute ethanol, magnetically stir at room temperature to completely dissolve, and monitor by TLC reaction process. After reacting at room temperature for 24 hours, the solvent ethanol was distilled off to obtain the crude product, and then a developing solvent with a volume ratio of petroleum ether / ethyl acetate of 100 / 1 was used to obtain 9-((4-methylphenyl) by column chromatography. Thio)-9H-xanthene, white solid. The yield of this step was 84% ​​(51 mg).

[0054] Product NMR verification results are as follows (see figure 1 and figure 2 ).

[0055] 1 H NMR (400MHz, CDCl 3 )δ7.29(d,J=7.6Hz,2H),7.24–7.20(m,2H),7.08–7.04(m,2H),6.97–6.91(m,4H),6.82(d,J=8.0Hz ,2H...

Embodiment 2

[0057] Example 2 Synthesis of 9-((4-ethylphenyl)thio)-9H-oxanthene

[0058] The structure of 9-((4-ethylphenyl)thio)-9H-xanthene is shown below:

[0059]

[0060] The specific preparation process is as follows: put 55.2mg of p-ethylthiophenol (0.4mmol) and 36.4mg of xanthene (0.2mmol) into 15mL Schlenk, add 2mL of absolute ethanol, stir magnetically at room temperature to completely dissolve, and monitor by TLC reaction process. After reacting at room temperature for 24 hours, the solvent ethanol was distilled off to obtain the crude product, and then a developing solvent with a volume ratio of petroleum ether / ethyl acetate of 100 / 1 was used to obtain 9-((4-ethylphenyl) by column chromatography. Sulfuryl)-9H-xanthene, colorless oily liquid. The yield of this step was 87% (55.3mg).

[0061] Product NMR verification results are as follows (see image 3 and Figure 4 ).

[0062] 1 H NMR (400MHz, CDCl 3 )δ7.29–7.25(m,2H),7.21(t,J=8.5Hz,2H),7.04(t,J=8.0Hz,2H),6.95(t,J=6....

Embodiment 3

[0064] Example 3 Synthesis of 9-((4-isopropylphenyl)thio)-9H-oxanthene

[0065] The structure of 9-((4-isopropylphenyl)thio)-9H-xanthene is shown below:

[0066]

[0067] The specific preparation process is as follows: put 60.8mg of p-isopropylthiophenol (0.4mmol) and 36.4mg of xanthene (0.2mmol) into 15mL Schlenk, add 2ml of absolute ethanol, stir magnetically at room temperature to completely dissolve, and pass TLC Monitor the progress of the reaction. After reacting at room temperature for 24 hours, the solvent ethanol was distilled off to obtain the crude product, and then the developing solvent with sherwood oil / ethyl acetate volume ratio of 100 / 1 was obtained by column chromatography to obtain 9-((4-isopropylphenyl )thio)-9H-xanthene, light yellow oily liquid. The yield of this step was 90% (59.7mg).

[0068] Product NMR verification results are as follows (see Figure 5 and Figure 6 ).

[0069] 1 H NMR (400MHz, CDCl 3 )δ7.26–7.19(m,4H),7.03(t,J=6.9Hz,2H),6.9...

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Abstract

The invention discloses a preparation method of a thioether compound. The thioether compound has a structural formula (I). According to the thioether compound, xanthene and a component in the description are taken as raw materials, mixed and dissolved in a solvent, the mixture is subjected to an open reaction at the room temperature, and a target product can be obtained; the solvent is an inert solvent with good compatibility with a raw material, wherein R<1>, R<2> and R<3> are independently selected from hydrogen, C1-C4 alkyl, C1-C4 alkoxy, halogen or hydroxy. According to the method, air istaken as an oxidizing agent, the two raw materials are subjected to a one-step reaction at the normal temperature under the normal pressure, and the thioether compound can be prepared simply. The whole reaction process is simple, the condition is mild, no catalyst or ligands are required to be added, side reactions in the reaction process are avoided, the product purity is high, the substrate application range is wide, the chemical selectivity is good, following further conversion is facilitated, the thioether compound has very good atom economy, the preparation method is suitable for large-scale production at a low cost, and popularization and application of the thioether compound are facilitated.

Description

technical field [0001] The invention relates to the field of organic synthesis, more specifically, to a preparation method of thioether compounds. Background technique [0002] Sulfur is a ubiquitous distributed element and is essential in all known organisms. According to the iron-sulfur world hypothesis, it even played a key role in the evolution of life. Many important biochemical processes in prokaryotic and eukaryotic cells are closely related to this special element. Enzymes not only contain iron-sulfur clusters but also rely on sulfur-containing cofactors such as thiamine, molybdenum phthalocyanine, biotin, and lipoic acid. In addition, many biosynthetic building blocks are activated as coenzyme A thioesters, which are associated with sulfur in some important detoxification processes, such as the conversion of cyanide to isothiocyanate and the conjugation of electrophilic toxins to glutathione and related compounds. related. Thio modification is also important for...

Claims

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Application Information

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IPC IPC(8): C07D311/84
CPCC07D311/84
Inventor 余国典陈迁王肖峰温春晓区颖聪
Owner GUANGDONG UNIV OF TECH
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