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A kind of synthetic method of aryl sulfide compound

A synthesis method and technology of aryl sulfide, which are applied in chemical instruments and methods, organic compound/hydride/coordination complex catalyst, sulfide preparation, etc., can solve the problems of cumbersome reaction, complicated post-processing, etc., and achieve product The effect of high yield and purity, short reaction time and mild reaction conditions

Inactive Publication Date: 2015-10-14
广州巴陶拜化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] As mentioned above, although there are many preparation methods of aryl sulfide compounds in the prior art, these methods still have certain defects, such as complex reactions, complicated post-treatment and many other shortcomings.

Method used

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  • A kind of synthetic method of aryl sulfide compound
  • A kind of synthetic method of aryl sulfide compound
  • A kind of synthetic method of aryl sulfide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 1: 1,3-dimethoxy-2-phenylthiobenzene

[0041]

[0042]At room temperature, add 100ml solvent methanol into the reactor, then add 20mmol formula (II) compound, 20mmol formula (III) compound, 1mmol above-mentioned formula (1) copper catalyst and 0.5mmol above-mentioned organic ligand L1, then heat up under stirring, The reaction was stirred at 60°C for 5 hours.

[0043] After the reaction is over, use a rotary evaporator to remove the solvent from the reaction system mixture obtained after the end of the reaction, and the residue is purified by 200-300 mesh silica gel column chromatography, using acetone and ethyl acetate with a volume ratio of 1:2:1 , n-hexane as the eluent, collect the eluted fractions, evaporate again to remove the eluent, and obtain the title product as a colorless oil, with a yield of 99.2%, and a purity of 98.8% as detected by high performance liquid chromatography .

[0044] NMR: 1 H NMR (CDCl 3 ,500MHz):δ3.77(s,6H),6.49(d,J=9.1Hz,2H...

Embodiment 2

[0045] Example 2: 1,2,3-trimethoxy-4-p-fluorophenylthiobenzene

[0046]

[0047] At room temperature, add 100ml solvent tetrahydrofuran into the reactor, then add 20mmol formula (II) compound, 30mmol formula (III) compound, 1.5mmol above-mentioned formula (1) copper catalyst and 1.5mmol above-mentioned organic ligand L1, then heat up under stirring , and the reaction was stirred at 70 °C for 4 hours.

[0048] After the reaction is over, use a rotary evaporator to remove the solvent from the reaction system mixture obtained after the end of the reaction, and the residue is purified by 200-300 mesh silica gel column chromatography, using acetone and ethyl acetate with a volume ratio of 1:2:1 , n-hexane mixture as the eluent, collect the eluted fractions, evaporate again to remove the eluent, and obtain the title product as a colorless solid with a yield of 97.9%, and its purity is 98.3% as detected by high performance liquid chromatography .

[0049] NMR: 1 H NMR (CDCl 3 ...

Embodiment 3

[0050] Example 3: 1,3-dimethoxy-2-p-nitrophenylthiobenzene

[0051]

[0052] At room temperature, add 100ml solvent DMF in the reactor, then add 20mmol formula (II) compound, 40mmol formula (III) compound, 2mmol above-mentioned formula (1) copper catalyst and 3mmol above-mentioned organic ligand L1, then heat up under stirring, in The reaction was stirred at 80°C for 3 hours.

[0053] After the reaction is over, use a rotary evaporator to remove the solvent from the reaction system mixture obtained after the end of the reaction, and the residue is purified by 200-300 mesh silica gel column chromatography, using acetone and ethyl acetate with a volume ratio of 1:2:1 , n-hexane mixture as the eluent, collect the eluted components, evaporate again to remove the eluent, and obtain the title product as a colorless solid with a yield of 97.6%, and its purity is 98.6% after detection by high performance liquid chromatography .

[0054] NMR: 1 H NMR (CDCl 3 ,500MHz):δ3.80(s,6H)...

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Abstract

The invention relates to a method for synthesizing an aryl thioether compound. The method comprises the step of carrying out one-step synthesis on an alkoxy-substituted halogenated aryl compound and an aryl thiol compound to obtain the aryl thioether compound in the presence of a catalyst and an organic ligand. The obtained product has the characteristics of high yield rate and high purity, thus a novel and efficient chemical synthesis method is provided to the preparation of the compounds and has good industrialization prospects and potential application values in fields of pharmaceutical intermediates industry, pesticides and the like.

Description

technical field [0001] The invention relates to a synthesis method of a sulfur-containing compound, in particular to a synthesis method of an aryl sulfide compound, and belongs to the field of organic chemical synthesis. Background technique [0002] So far, it has been found that sulfur-containing compounds can play an important role in many chemical fields such as organic synthesis, medicine, pesticides, and resin synthesis, and can serve as various organic synthesis intermediates and final active compounds. [0003] Among sulfur compounds, aryl sulfide compounds play an important role. Aryl sulfide compounds have specific biological activity, pharmaceutical activity, etc., and can become the basic fragment unit in a variety of clinical drug molecules, based on which a variety of pharmaceutical compounds with different therapeutic uses can be synthesized, such as: [0004] CN1721401A discloses an aryl sulfide compound, which can be used as an inhibitor of leukocyte functi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C319/14C07C323/20B01J31/22
Inventor 李娜
Owner 广州巴陶拜化工有限公司