Thioether compound, preparation method thereof, medical intermediate and application thereof

A compound and thioether technology, applied in the field of thioether compounds and their preparation, can solve problems such as metal residues, and achieve the effects of eliminating metal residues, high yield and simple operation

Active Publication Date: 2020-08-11
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the embodiments of the present invention is to provide a thioether compound to solve the problem that the existing thioether compound proposed in the above background technology needs to use a transition metal for catalytic reaction during synthesis, and the synthesized product is prone to metal residues.

Method used

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  • Thioether compound, preparation method thereof, medical intermediate and application thereof
  • Thioether compound, preparation method thereof, medical intermediate and application thereof
  • Thioether compound, preparation method thereof, medical intermediate and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] A thioether compound 001, namely the thioether compound numbered 001, the specific structural formula is:

[0046]

[0047] In this example, the specific synthesis steps of the thioether compound 001 are as follows:

[0048] At room temperature, 1-(tert-butyl)-4-(methylsulfoxide)benzene (60.1 mg, 0.3 mmol), methyl bromoacetate (281.0 mg , 1.8mmol), while adding 0.15mL of 1-butyl-3-methylimidazolium trifluoromethanesulfonate, then placed on a reactor at 100°C for 48h; the reaction system after the reaction was cooled to room temperature ( Usually 25 ℃), after the cooling is completed, the reaction system is washed with water, then extracted three times with ethyl acetate, the organic phase of the three extractions is combined into a 50mL eggplant-shaped bottle, and the Heidolph rotary evaporator (rotating speed is 90rpm, temperature is 40°C, vacuum degree is 0.1Mpa) rotary evaporation treatment for 3min, the residue was separated by column chromatography using 200 me...

Embodiment 2

[0054] A thioether compound 002, namely the thioether compound numbered 002, the specific structural formula is:

[0055]

[0056] In this example, the specific synthesis steps of the thioether compound 002 are as follows:

[0057] Add 1-bromo-3-(methylsulfoxide)benzene (67.1mg, 0.3mmol), methyl bromoacetate (281.0mg, 1.8mmol) sequentially to a 4mL pre-dried vial at room temperature , while adding 0.15 mL of 1-butyl-3-methylimidazolium trifluoromethanesulfonate, and then placed on a reactor at 100 ° C for 48 h; the reaction system after the reaction was cooled to room temperature (usually 25 ° C ), after the cooling was completed, the reaction system was washed with water, then extracted three times with ethyl acetate, and the organic phases extracted three times were combined into a 50mL eggplant-shaped flask, and the Heidolph rotary evaporator (rotating speed was 90rpm, temperature was 40°C, vacuum degree of 0.1Mpa) rotary steaming treatment for 3min, the residue was sep...

Embodiment 3

[0063] A thioether compound 003, namely the thioether compound numbered 003, the specific structural formula is:

[0064]

[0065] In this example, the specific synthesis steps of the thioether compound 003 are as follows:

[0066] At room temperature, add 4-(methylsulfoxide)benzaldehyde (51.5mg, 0.3mmol) and methyl bromoacetate (281.0mg, 1.8mmol) successively to a pre-dried vial with a capacity of 4mL, and add 0.15mL of 1-butyl-3-methylimidazolium trifluoromethanesulfonate, then placed in a reactor at 100°C for 48h; the reaction system after the reaction was cooled to room temperature (usually 25°C), cooled After completion, the reaction system was washed with water, and then extracted three times with ethyl acetate, and the organic phases extracted three times were combined into a 50 mL eggplant-shaped flask, and the Heidolph rotary evaporator (90 rpm, 40 °C, and 0.1 Mpa) rotary steaming treatment for 3min, the residue was separated by column chromatography using 200 mes...

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Abstract

The invention relates to the technical field of chemical synthesis, and particularly discloses a thioether compound, a preparation method of the thioether compound, a medical intermediate and application of the medical intermediate, and the thioether compound is prepared from the following raw materials: a sulfoxide compound, a bromide and 1-butyl-3-methylimidazole trifluoromethanesulfonate. The thioether compound provided by the invention is reacted in ionic liquid 1-butyl-3-methylimidazole trifluoromethanesulfonate, a metal catalytic reaction is not needed, the problems of metal residues, organic solvent pollution and the like are fundamentally eliminated, and the thioether compound is particularly suitable for synthesis of some medicines and has relatively high economic applicability. The preparation method provided by the invention has the advantages of simple operation, high yield, high product purity, no need of metal catalysis in the whole reaction, mild reaction conditions andwide substrate range, solves the problem of easy generation of metal residues in the synthesized product due to use of transition metals for catalytic reaction in synthesis of thioether compounds in the prior art, and has a wide market prospect.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a thioether compound and its preparation method, a pharmaceutical intermediate and its application. Background technique [0002] Thioether compounds generally refer to compounds containing R-S-R groups, wherein R is an organic group. Under the influence of sulfur atoms in thioether compounds, α-carbon atoms can form carbon positive, negative ions or carbon free radicals, which can carry out a variety of chemical reactions, and are widely used in life sciences, chemicals, medicine and other fields scope. [0003] At present, the main synthesis method of thioether compounds is: sulfoxide compounds are used as raw materials to reduce thioethers. This kind of reaction uses sulfoxide compounds as raw materials, and the combination of transition metals and expensive and complex ligands is used to catalyze the reduction of sulfoxides to Thioether. For example, in the prio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/52C07C319/14
CPCC07C323/52
Inventor 刘辰婧傅元媛朱圣臻陈登峰孟祥太张颖茵罗金岳黄申林
Owner NANJING FORESTRY UNIV
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