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Method for synthesizing oxime ether compound based on C-N bond breakage

A synthesis method and compound technology are applied in the fields of pharmaceutical chemical intermediates and related chemistry to achieve the effects of wide substrate range, easy product and mild reaction conditions

Inactive Publication Date: 2016-12-07
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the traditional synthetic method has been used until now, there are still many limitations in the application of many substrates

Method used

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  • Method for synthesizing oxime ether compound based on C-N bond breakage
  • Method for synthesizing oxime ether compound based on C-N bond breakage
  • Method for synthesizing oxime ether compound based on C-N bond breakage

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1: Synthesis of 1-(4-ethoxyphenyl)ethanone O-methyl oxime (1a)

[0035]

[0036] Add p-ethoxyacetophenone (0.75mmol, 127mg), N-methoxybenzamide (0.5mmol, 78.2mg), potassium persulfate (1.0mmol, 270.3mg), anhydrous methanol 2mL into the reactor , sealed, and stirred at 80°C for 20 hours. Cool to room temperature, remove the solvent under reduced pressure, separate and purify by column chromatography (eluent: petroleum ether / ethyl acetate=600:1) to obtain 90.8 mg of 1-(4-ethoxyphenyl)ethanone O-methyl oxime (1a) , yield 94%.

[0037] 1 H NMR (400MHz, CDCl 3 ): δ7.58(d, J=8.5Hz, 2H), 6.87(d, J=8.5Hz, 2H), 4.04(q, J=7.0Hz, 2H), 3.97(s, 3H), 2.19(s ,3H),1.41(t,J=7.0Hz,3H); 13 C NMR (100MHz, CDCl 3 ): δ159.8, 154.3, 129.0, 127.3, 114.3, 63.5, 61.8, 14.8, 12.5.

Embodiment 2

[0038] Example 2: Synthesis of 1-(4-ethoxyphenyl)ethanone O-methyl oxime (1a)

[0039]

[0040] Add p-ethoxyacetophenone (0.75mmol, 127mg), N-methoxybenzamide (0.5mmol, 78.2mg), sodium persulfate (1.0mmol, 238.1mg), anhydrous methanol 2mL into the reactor , sealed, and stirred at 80°C for 20 hours. Cool to room temperature, remove the solvent under reduced pressure, and separate and purify by column chromatography (eluent: petroleum ether / ethyl acetate=600:1) to obtain 45.1 mg of 1-(4-ethoxyphenyl)ethanone O-methyl oxime (1a) , yield 47%.

Embodiment 3

[0041] Example 3: Synthesis of 1-(4-ethoxyphenyl)ethanone O-methyl oxime (1a)

[0042]

[0043]Add p-ethoxyacetophenone (0.75mmol, 127mg), N-methoxybenzamide (0.5mmol, 78.2mg), potassium persulfate (1.0mmol, 270.3mg), absolute ethanol 2mL into the reactor , sealed, and stirred at 80°C for 20 hours. Cool to room temperature, remove the solvent under reduced pressure, and separate and purify by column chromatography (eluent: petroleum ether / ethyl acetate=600:1) to obtain 26.1 mg of 1-(4-ethoxyphenyl)ethanone O-methyl oxime (1a) , yield 27%.

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Abstract

The invention relates to a method for synthesizing an oxime ether compound based on C-N bond breakage. The method comprises the step of making a compound shown in equation (1) and a compound show in equation (2) react in the presence of peroxide and an organic solvent to obtain the oxime ether compound as shown in formula (3), and reaction expression is shown in the description. According to the method, synthesis path is short, starting materials are simple, reaction condition is mild, the peroxide is cheap and free of pollution, substrate range is wide, products are easy to separate, and adaptability is high when reaction is amplified to be at the gram grade.

Description

technical field [0001] The invention belongs to the field of pharmaceutical and chemical intermediates and related chemical technologies, and specifically relates to a green synthesis method of various oxime ether compounds. Background technique [0002] Oxime ether compounds are widely used in the field of chemistry. The skeleton structure of their compounds can often be found in molecular structures such as drugs, natural active products, and agricultural chemicals. It can be seen that the skeleton of oxime ether compounds has broad scientific research value and market prospects. [0003] Common oxime ether compounds have a traditional synthesis method, which can be roughly divided into two types: one method is to use a compound containing a carbonyl or aldehyde functional group to directly react with an alkoxy-substituted primary amine hydrochloride, which can directly generate Oxime ether compounds. Another method is to use a compound containing a carbonyl or aldehyde f...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C249/04C07C251/48C07C315/04C07C317/32C07C253/30C07C255/62
CPCC07C249/04C07C253/30C07C315/04C07C251/48C07C317/32C07C255/62
Inventor 王彬宋栗
Owner NANKAI UNIV
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