Method for synthetizing mono-thioether compound

A compound, monosulfide technology, applied in the field of synthesizing monosulfide compounds, can solve problems such as complex operation methods, achieve low process difficulty, facilitate large-scale industrial production, and be easy and safe to operate

Inactive Publication Date: 2012-08-01
LIAONING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The general operation methods of the above synthetic methods are relatively complicated, and the reaction conditions are relatively strict.

Method used

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  • Method for synthetizing mono-thioether compound
  • Method for synthetizing mono-thioether compound
  • Method for synthetizing mono-thioether compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Add furfuryl disulfide (2mmol), bromo-n-pentane (4.2mmol), selenium powder (0.2mmol), H 2 O (50 mmol), NaOAC (1.25 mmol) and solvent DMF (20 ml), continue to feed carbon monoxide, under normal pressure, heat to 90oC and stir for 5 hours, after cooling to room temperature, switch carbon monoxide to air, and stir for 0.5-1 After one hour, the selenium powder was filtered out, the filtrate was extracted with distilled water and cyclohexane respectively, and the solvent in the extract was distilled off under reduced pressure to obtain the target product with a yield of 80.9%.

[0021]

Embodiment 2

[0023] The method is the same as in Example 1, the yields for different substrates are as follows, and the product is verified by NMR, and the structural formula is as follows

[0024]

[0025]

[0026]

[0027]

[0028]

Embodiment 3

[0030] Method is with embodiment 1, only changes the consumption of catalyst selenium, and yield is as follows:

[0031] Selenium dosage (mmol) 0.02 0.10 0.16 0.20 0.24 0.30 0.40 Percentage of selenium relative to furfuryl disulfide % 1 5 8 10 12 15 20 Yield % 74 85 90 80.9 89 87 90

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Abstract

The invention relates to a method for synthetizing mono-thioether compound. The technical scheme adopted by the invention is as follows: in the presence of carbon monoxide and water, disulfide compound and halogenated hydrocarbon compound are used as raw materials, selenium is used as catalyst, organic base or inorganic base is used as cocatalyst or any cocatalyst is not added, the raw materials react in organic solvent at 20-100 DEG C under atmospheric pressure for 1-24 hours, the product is cooled to the room temperature, then carbon monoxide is displaced by air, stirring is performed for 0.2-2 hours, filtration is performed, distilled water and cyclohexane are used to extract the filtrate, and the solvent in the extract liquor is distilled out through reduced pressure distillation to obtain the target product. The method is convenient and safe to operate, adopts one-pot reaction, has common raw materials, no pollution, high selectivity and high yield; and the catalyst can be separated and recycled after the reaction.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a method for synthesizing monosulfide compounds through selenium-catalyzed reaction by using disulfide compounds and halogenated hydrocarbons as raw materials, utilizing carbon monoxide and water. Background technique [0002] Monosulfide compounds are important fine chemical raw materials and organic synthesis intermediates. Thioether is not only a raw material for organic synthesis, but also a good solvent and extractant for extracting rare metals and precious metals (such as Au, Pd, Ag, etc.). Thioether is widely used in the fields of organic synthesis, medicine, pesticides, dyes, and food additives. At the same time, thioether is an important class of spices. Furfuryl sulfide has coffee or sesame oil aroma, and furfuryl pentyl sulfide has fruity aroma. Furfuryl benzyl sulfide has a burnt coffee aroma. Thioether can be synthesized by a variety of methods: the ea...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/38C07C323/09C07C319/14
Inventor 刘晓智龙慎杰毛颖刁海倩孔庆文王月娇郭福顺
Owner LIAONING UNIVERSITY
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