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Method for synthesizing N-substituted sulfimide compounds

A sulfimide and compound technology, applied in the field of metal-catalyzed organic synthesis, can solve the problems of complex reaction conditions, cumbersome raw material synthesis steps, low reaction efficiency, etc., and achieves simple raw material synthesis, wide application range of substrates, and high reaction efficiency. Effect

Active Publication Date: 2020-12-01
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0019] In the above-mentioned technical solutions, there are situations such as cumbersome raw material synthesis steps, low reaction efficiency, and complicated reaction conditions.

Method used

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  • Method for synthesizing N-substituted sulfimide compounds
  • Method for synthesizing N-substituted sulfimide compounds
  • Method for synthesizing N-substituted sulfimide compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042]

[0043] A method for synthesizing N-substituted sulfimide compounds, comprising the following steps:

[0044] In air atmosphere, with N-(hydrocarbonyloxy) amides and disubstituted thioethers as raw materials, toruthenium The complex is a catalyst, reacts in a reaction solvent in the presence of a silver salt additive and a ligand, and after the reaction is separated by column chromatography to obtain N-substituted sulfimide compounds, wherein:

[0045] The structural formula of the N-(hydrocarbyloxy) amides is in:

[0046] R 1 is aryl;

[0047] R 2 is pivaloyl;

[0048] The structural formula of disubstituted thioethers is in:

[0049] R 3 is phenyl;

[0050] R 4 is benzyl;

[0051] The molar ratio of the N-(hydrocarbyloxy)amide, disubstituted thioether, ruthenium complex, silver salt additive, and ligand is 1:1:0.01:0.04:0.02;

[0052] The amount of reaction solvent used was 5 mL / g based on the weight of N-(hydrocarbyloxy)amide.

[0053] Further, the ...

Embodiment 2

[0063]

[0064] A method for synthesizing N-substituted sulfimide compounds, comprising the following steps:

[0065] In air atmosphere, take N-(hydrocarbonyloxy) amides and disubstituted sulfides as raw materials, use ruthenium complexes as catalysts, and react in a reaction solvent in the presence of silver salt additives and ligands, and the reaction ends After recrystallization, N-substituted sulfimide compounds are obtained, wherein:

[0066] The structural formula of the N-(hydrocarbyloxy) amides is in:

[0067] R 1 is an aryl group containing a substituent, and the substituent is chlorine;

[0068] R 2 is pivaloyl;

[0069] The structural formula of disubstituted thioethers is

[0070] R 3 is phenyl;

[0071] R 4 is benzyl;

[0072] The N-(hydrocarbyloxy) amides, disubstituted thioethers, ruthenium The molar ratio of complex, silver salt additive and ligand is 1:2:0.1:0.4:0.2;

[0073] The amount of reaction solvent used was 25 mL / g based on the weight...

Embodiment 3

[0083]

[0084] A method for synthesizing N-substituted sulfimide compounds, comprising the following steps:

[0085] In air atmosphere, with N-(hydrocarbonyloxy) amides and disubstituted thioethers as raw materials, to ruthenium The complex is a catalyst, reacts in a reaction solvent in the presence of a silver salt additive and a ligand, and after the reaction is separated by column chromatography to obtain N-substituted sulfimide compounds, wherein:

[0086] The structural formula of the N-(hydrocarbyloxy) amides is in:

[0087] R 1 is an aryl group containing a substituent, and the substituent is F;

[0088] R 2 is pivaloyl;

[0089] The structural formula of disubstituted thioethers is in:

[0090] R 3 is phenyl;

[0091] R 4 is benzyl;

[0092] The N-(hydrocarbyloxy) amides, disubstituted thioethers, ruthenium The molar ratio of complex, silver salt additive and ligand is 1:1.5:0.05:0.2:0.1;

[0093] The amount of the reaction solvent used was 10 mL / g b...

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Abstract

The invention discloses a method for synthesizing N-substituted sulfimide compounds. The preparation method comprises the following steps: in an air atmosphere, taking N-(hydrocarbon acyloxy) amide and disubstituted thioether as raw materials, taking a ruthenium complex as a catalyst, reacting in a reaction solvent in the presence of a silver salt additive and a ligand, and after the reaction is finished, separating and purifying to obtain the N-substituted sulfimide compounds. The method has the beneficial effects that (1) through comprehensive screening and cooperation of a proper substrate,temperature, the catalyst and the ligand, the application range of the substrate is wide; and (2) compared with the existing method, the method has the advantages of simple raw material synthesis, mild reaction conditions, no need of inert gas protection, simple operation and high reaction efficiency.

Description

technical field [0001] The invention relates to a method for synthesizing N-substituted sulfimide compounds, belonging to the field of metal-catalyzed organic synthesis. Background technique [0002] Sulfionimide is a monoaza analogue of sulfoxide, and many derivatives have important biological activities, which are of great significance in medicinal chemistry and crop protection. In the published synthetic methods, it is usually necessary to use a suitable nitrene precursor in combination with a thioether to obtain different sulfimide derivatives, for example: [0003] D. Swern (D.Swern) et al. ("Tetracovalent Sulfur intermediates iniminosulfurane synthesis", Tetrahedron Lett., 1972,13, 2635-2638.) disclose a kind of under the effect of tert-butyl hypochlorite, sulfur The ether is converted into the target product, and the reaction formula is as follows: [0004] [0005] E.M. Carreir (E.M.Carreir) et al. ("N,O-Bis(trifluoroacetyl)hydroxylamine asa Useful Electrophilic...

Claims

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Application Information

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IPC IPC(8): C07C381/10
CPCC07C381/10
Inventor 夏远志张鑫羽陈建辉罗燕书陈佳佳
Owner WENZHOU UNIVERSITY