A kind of thioether compound and its preparation method, pharmaceutical intermediate and its application

A compound and thioether technology, which is applied in the field of thioether compounds and their preparation, can solve problems such as metal residues, achieve the effects of eliminating metal residues, mild reaction conditions, and simple operation

Active Publication Date: 2022-06-21
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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  • A kind of thioether compound and its preparation method, pharmaceutical intermediate and its application
  • A kind of thioether compound and its preparation method, pharmaceutical intermediate and its application
  • A kind of thioether compound and its preparation method, pharmaceutical intermediate and its application

Examples

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Embodiment 1

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

[0046]

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

[0048] 1-(tert-Butyl)-4-(methylsulfoxide)benzene (60.1 mg, 0.3 mmol), followed by methyl bromoacetate (281.0 mg) were added to a 4 mL pre-dried vial at room temperature. , 1.8 mmol), at the same time, 0.15 mL of 1-butyl-3-methylimidazole trifluoromethanesulfonate was added, and then placed in a reactor at 100 ° C for 48 h; the reaction system after the reaction was cooled to room temperature ( Usually 25°C), after cooling, 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 50 mL eggplant-shaped bottle, and a Heidolph rotary evaporator (rotating speed was 90 rpm, temperature was 40 ℃, vacuum degree is 0.1Mpa) rotary evaporation for 3min, th...

Embodiment 2

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

[0055]

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

[0057] 1-Bromo-3-(methylsulfoxide)benzene (67.1 mg, 0.3 mmol), followed by methyl bromoacetate (281.0 mg, 1.8 mmol) were added to a 4 mL pre-dried vial at room temperature. , at the same time, 0.15 mL of 1-butyl-3-methylimidazole trifluoromethanesulfonate was added, and then placed in a reactor at 100 ° C for 48 h; the reaction system after the reaction was cooled to room temperature (usually 25 ° C ), the reaction system was washed with water after cooling, and then extracted three times with ethyl acetate, and the organic phase extracted three times was merged into a 50 mL eggplant-shaped flask, and a Heidolph rotary evaporator (rotating speed was 90 rpm, temperature was 40 ° C, vacuum 0.1Mpa) rotary evaporation for 3min, the residue was separated...

Embodiment 3

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

[0064]

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

[0066] 4-(Methylsulfoxide)benzaldehyde (51.5 mg, 0.3 mmol), methyl bromoacetate (281.0 mg, 1.8 mmol) were sequentially added to a pre-dried vial with a capacity of 4 mL at room temperature, and simultaneously 0.15mL of 1-butyl-3-methylimidazole trifluoromethanesulfonate, and 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 the completion, 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 50 mL eggplant-shaped bottle, and a Heidolph rotary evaporator (rotation speed was 90 rpm, temperature was 40 ° C, and vacuum degree was 0.1 Mpa) rotary evaporati...

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Abstract

The invention relates to the technical field of chemical synthesis, and specifically discloses a thioether compound and a preparation method thereof, a pharmaceutical intermediate and its application. The thioether compound includes the following raw materials: sulfoxide compound, bromide and 1- Butyl-3-methylimidazolium triflate. The thioether compounds provided by the present invention are reacted in the ionic liquid 1-butyl-3-methylimidazolium trifluoromethanesulfonate without using metal-catalyzed reactions, and fundamentally eliminate the problems of metal residues and organic solvent pollution. , especially suitable for the synthesis of some drugs, and has high economic applicability. The preparation method provided is simple in operation, high in yield, high in product purity, the whole reaction does not require metal catalysis, and at the same time, the reaction conditions are mild and the substrate range is wide, which solves the problem that the existing thioether compounds need to use transition metals for catalytic reactions in the synthesis. , there is a problem that the synthesized product is prone to metal residues, and has a broad market prospect.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a thioether compound and a preparation method thereof, a pharmaceutical intermediate and applications thereof. Background technique [0002] Thioether compounds generally refer to compounds containing R-S-R groups, wherein R is an organic group. Due to the influence of sulfur atoms in sulfide compounds, α-carbon atoms can form carbon positive, negative ions or carbon free radicals, so that various chemical reactions can be carried out, and they are widely used in life science, chemical industry, medicine and other fields. scope. [0003] At present, the main synthesis methods of sulfide compounds are as follows: sulfoxide compounds are used as raw materials to reduce sulfides to form sulfides. In this type of reactions, sulfoxide compounds are used as raw materials, and transition metals are combined with expensive and complex ligands to catalyze the reduction of sulf...

Claims

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Application Information

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Patent Type & Authority Patents(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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