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Electrochemical oxidation synthesis method for amide and application thereof

A technology of oxidative synthesis and synthesis method, applied in electrolysis process, electrolysis components, electrolysis organic production and other directions, can solve the problems of toxic activation reagents, expensive catalysts, etc., and achieve the effects of less by-products, high yield, and mild reaction conditions

Inactive Publication Date: 2019-02-12
SOUTHWEST UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these reported strategies are quite effective, these strategies still have some shortcomings, such as: many activating reagents are toxic and require stoichiometric amounts, some require metals, and some require expensive catalysts

Method used

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  • Electrochemical oxidation synthesis method for amide and application thereof
  • Electrochemical oxidation synthesis method for amide and application thereof
  • Electrochemical oxidation synthesis method for amide and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] The effect of different dielectrics on the electrochemical oxidation of amides:

[0032] The general reaction formula is as figure 1 Shown:

[0033] (1) Electrochemical oxidation: First, add 1mmol of potassium thioacetate and 0.5mmol of aniline into the reaction test tube, add 0.50mmol of tetrabutylammonium tetrafluoroborate as the electrolyte, and 5.0mL of acetonitrile as the solvent and stirring bar. Install two 1.0cm×1.0cm platinum electrodes in the test tube as the cathode and anode respectively, and react for 24 hours after passing a current of 1.0mA;

[0034] (2) washing and drying: the mixture after the reaction is filtered, and the filtrate is successively washed with saturated NaHCO 3 Solution, saturated brine and pure water were washed and extracted, and the organic phase after washing and extraction was dried with anhydrous sodium sulfate and then rotary evaporated to obtain a crude product;

[0035] (3) Purification of amide compound: the crude product i...

Embodiment 2

[0039] Effects of different organic solvents on the synthesis of amides by electrochemical oxidation:

[0040] (1) Electrochemical oxidation: first, add 1 mmol of potassium thioacetate and 0.5 mmol of aniline into the reaction test tube, add 0.50 mmol of tetrabutylammonium tetrafluoroborate as electrolyte, and 5.0 mL of dichloromethane as solvent and stirring bar, Install two 1.0cm×1.0cm platinum electrodes in the reaction test tube as the cathode and anode respectively, and react for 24 hours after passing a current of 1.0mA;

[0041] (2) washing and drying: the mixture after the reaction is filtered, and the filtrate is successively washed with saturated NaHCO 3 Solution, saturated brine and pure water were washed and extracted, and the organic phase after washing and extraction was dried with anhydrous sodium sulfate and then rotary evaporated to obtain a crude product;

[0042] (3) Purification of amide compound: the crude product was purified by column chromatography, an...

Embodiment 3

[0045] (1) Electrochemical oxidation: first, add 1mmol of potassium thioacetate and 0.5mmol of aniline into the reaction test tube, add 0.50mmol of tetrabutylammonium tetrafluoroborate as electrolyte, 5.0mL of ethyl acetate as solvent and stirring bar, Install two 1.0cm×1.0cm platinum electrodes in the reaction test tube as cathode and anode respectively, and react for 12h after passing a current of 12.0mA;

[0046] (2) washing and drying: the mixture after the reaction is filtered, and the filtrate is successively washed with saturated NaHCO 3 Solution, saturated brine and pure water were washed and extracted, and the organic phase after washing and extraction was dried with anhydrous sodium sulfate and then rotary evaporated to obtain a crude product;

[0047] (3) Purification of amide compound: the crude product was purified by column chromatography, and the eluent was a mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 2:1 to obtain the amide produc...

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Abstract

The invention discloses an electrochemical oxidation synthesis method for amide and application thereof, and belongs to the technical field of electrochemical organic synthesis. According to the synthesis method for the amide, thiocarboxylic acid or thiocarboxylate and amine are adopted as reaction raw materials, firstly, the thiocarboxylic acid or the thiocarboxylate is oxidized through an anodein an electrolytic tank so as to form free radical intermediates, then the two free radical intermediates are coupled so as to form a key intermediate disulfide compound, and then nucleophilic addition-elimination reaction is carried out on the disulfide compound and the reactant amine so as to generate an amide compound. The synthesis method has the advantages that no catalyst needs to be added,in addition, the reaction conditions are mild, by-products are few, synthesis and purification of the amide compound are facilitated, and the method has wide application in preparation of amide drugsin drug synthesis.

Description

technical field [0001] The invention belongs to the technical field of electrochemical organic synthesis, and in particular relates to an electrochemical oxidation synthesis method of amides and its application. Background technique [0002] The amide bond is not only a part of the main skeleton structure of many natural products (such as: polypeptides, proteins and chitin), but also very important in many organic compounds (such as: catalysts, drugs, agricultural chemicals and organic functional materials) One of the functional groups. A 2006 survey found an amide bond in two-thirds of drug candidates; 24% of the top 200 drugs by prescription drug sales in 2016 contained an amide bond in their structure. The amide bond is a key structure in many high-selling drugs, such as: fentanyl, aripiprazole, imatinib, lidocaine, ambien and lenalidomide, the structural formula is as follows figure 2 shown. [0003] In the last decade, the use of thiocarboxylic acids as acyl sources ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C25B3/02C25B3/23
CPCC25B3/23
Inventor 官智唐立
Owner SOUTHWEST UNIVERSITY
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