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A kind of method for preparing n-sulfonimide

A technology of sulfonimide and sulfonamide, which is applied in the field of preparing N-sulfonimide, can solve problems such as unsuitability, and achieve the effects of less reaction steps, high atom economy, and cheap and easy-to-obtain raw materials

Active Publication Date: 2022-07-19
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Obviously not suitable for industrialization and synthesis of complex products (see : ACS Sustainable Chem. Eng. 2018 , 6, 8563 ）

Method used

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  • A kind of method for preparing n-sulfonimide
  • A kind of method for preparing n-sulfonimide
  • A kind of method for preparing n-sulfonimide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026]

[0027] To the tube was added amide (0.5 mmol), p-methoxybenzenesulfonamide (0.75 mmol), iron sulfate (20 % mmol), potassium bisulfate (2.0 eq), then cyclohexane (2 mL), and finally Ethyl diazoacetate EDA (3.0 mmol), and the mixture was reacted in an oil bath at 90°C for 24 hours under an air atmosphere. After the reaction was completed, it was quenched with saturated sodium chloride solution, extracted with ethyl acetate, the organic phases were combined, dried over anhydrous magnesium sulfate, and the solvent was spin-dried under reduced pressure. The product can be obtained by column chromatography with a mixed solvent of ethyl acetate and petroleum ether with a yield of 90%. The main test data of the obtained product are as follows. It can be seen from the analysis that the actual synthetic product is consistent with the theoretical analysis.

[0028] 1 H NMR (400 MHz, CDCl 3 ) δ 7.80–7.75 (m, 2H), 6.96–6.89 (m, 2H), 4.58(s, 2H), 4.05 (q, J = 7.1 Hz, 2H), 3...

Embodiment 2

[0030] On the basis of Example 1, the reaction conditions were changed by a single factor:

[0031] Without adding ferric sulfate, yield: 68%;

[0032] Without potassium hydrogen sulfate, yield: 35%;

[0033] Replace ferric sulfate with cobalt sulfate, yield: 67%;

[0034] Replace iron sulfate with cobalt acetylacetonate, yield: 32%;

[0035] Replace ferric sulfate with ferric acetylacetonate, yield: 67%;

[0036] Replace ferric sulfate with ferrous sulfate, yield: 70%;

[0037] Replace ferric sulfate with ferric oxide, yield: 65%;

[0038] Replace ferric sulfate with copper acetate, yield: 35%;

[0039] Replace potassium hydrogen sulfate with potassium dihydrogen phosphate, yield: 33%;

[0040] Replace potassium hydrogen sulfate with sodium dihydrogen phosphate, yield: 23%;

[0041] Replace cyclohexane with n-hexane, yield: 22%;

[0042] Replace cyclohexane with 1,4-dioxane, yield: 32%;

[0043] Replace cyclohexane with acetonitrile, yield: 38%;

[0044] Replace cyc...

Embodiment 3

[0048]

[0049]To the tube was added amide (0.5 mmol), sulfonamide (0.75 mmol), iron sulfate (20 % mmol), potassium bisulfate (2.0 eq), then cyclohexane (2 mL) and finally ethyl diazoacetate EDA (3.0 mmol), the mixture was reacted in an oil bath at 90 °C for 24 hours under an air atmosphere. After the reaction was completed, it was quenched with saturated sodium chloride solution, extracted with ethyl acetate, the organic phases were combined, dried over anhydrous magnesium sulfate, and the solvent was spin-dried under reduced pressure. The product was obtained by column chromatography with a mixed solvent of ethyl acetate and petroleum ether with a yield of 66%. The main test data of the obtained product are as follows. It can be seen from the analysis that the actual synthetic product is consistent with the theoretical analysis.

[0050] 1 H NMR (400 MHz, CDCl 3 ) δ 7.82 (d, J = 8.1 Hz, 2H), 7.76 (d, J = 8.9Hz, 2H), 7.25 (d, J = 8.1 Hz, 2H), 6.89 (d, J = 8.9 Hz...

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Abstract

The invention discloses a method for preparing N-sulfonimide: using ferric sulfate as a catalyst or no catalyst, and potassium hydrogen sulfate as an auxiliary agent to realize the three-component reaction of amide, sulfonamide and ethyl diazoacetate to prepare N ‑Sulfonimide has the following advantages: cheap and green catalyst, more economical reaction, wide substrate versatility, readily available raw materials, can be carried out in the air, and simple post-processing, which is conducive to the synthesis of drug molecules and large-scale industrialization applications in . At the same time, the reactants, catalysts, assistants and the like used in the present invention are cheap and easy to obtain, the reaction composition is reasonable, no ligands and toxic metal catalysts are required, the atom economy is high, the reaction steps are few, and a higher reaction can be obtained only in one step. Yield, in line with the requirements and directions of contemporary green chemistry and medicinal chemistry.

Description

technical field [0001] The present invention relates to a preparation N -The method of sulfonimide belongs to the technical field of organic synthesis. Background technique [0002] N -Sulfonimide is widely present in drug molecules, natural products and pesticides, the core skeleton of functional materials, and is also widely used as a ligand molecule for transition metals. Currently, preparing N Although there are many methods for -sulfonimide, they all have obvious shortcomings, such as: the need to prepare dangerous azide compounds, the preparation of raw materials is cumbersome; the need for toxic and harmful transition metals and the like. E.g: [0003] (1) Chang's group reported the preparation from azides, alkynes and alcohols under the catalysis of cuprous iodide N - Sulfonimide works, but the reaction must use dangerous azides and toxic copper catalysts. Not suitable for large-scale industrial reactions and synthesis of drug molecules (see: Org. Lett., 2006 ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C311/51C07C303/40C07D209/26C07D333/60C07D209/42C07D261/20C07D333/34C07D471/04C07D231/12C07D493/14
CPCC07C303/40C07D209/26C07D333/60C07D209/42C07D261/20C07D333/34C07D471/04C07D231/12C07D493/14C07C311/51
Inventor 万小兵李晶晶赵彦伟杨金炜李如一曹志宇
Owner SUZHOU UNIV
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