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Etoxazole hapten, and synthesis method and application thereof

A synthesis method and etoxazole technology are applied in the field of etoxazole hapten and synthesis thereof, and achieve the effects of easy availability of raw materials, easy control of reaction conditions, and high purity and yield

Pending Publication Date: 2019-07-05
SHENZHEN BIOEASY BIOTECHNOLOGY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, at present, there is no relevant report on etoxazole hapten in China

Method used

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  • Etoxazole hapten, and synthesis method and application thereof
  • Etoxazole hapten, and synthesis method and application thereof
  • Etoxazole hapten, and synthesis method and application thereof

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preparation example Construction

[0036] In the second aspect, the present invention also provides a method for synthesizing the above-mentioned etoxazole hapten, comprising the following steps:

[0037] S1, providing intermediate 1 having the structural formula ;

[0038] S2, providing an intermediate 2 having the structural formula , wherein, n is the number of -CH2 groups, and n is an integer of 1-5;

[0039] S3, reacting the intermediate 1 and the intermediate 2 to obtain the intermediate 3, the intermediate 3 has the structural formula , wherein, n is the number of -CH2 groups, and n is an integer of 1-5;

[0040] S4, subjecting the intermediate 3 to a condensation reaction to obtain the intermediate 4, the intermediate 4 has the structural formula , wherein, n is the number of -CH2 groups, and n is an integer of 1-5;

[0041]S5, performing an oxidation reaction on the intermediate 4 to obtain the etoxazole hapten.

[0042] According to the structural characteristics of etoxazole, the invention ...

Embodiment 1

[0058] A synthetic method of etoxazole hapten, comprising the steps of:

[0059] S1, providing intermediate 1, wherein the preparation method of intermediate 1 is: add 2,6-difluorobenzamide and 2-chloroacetaldehyde dimethyl acetal to a one-necked bottle, and stir for 5 minutes under ice-water bath conditions , then slowly add concentrated sulfuric acid to it, after the dropwise addition, react overnight at room temperature, after the reaction, pour the reaction solution into ice water, stir well, extract 2-3 times with ethyl acetate, combine the organic phases, organic After washing and concentrating, the phase is purified by column to obtain intermediate 1; wherein, the ratio of the amount of substances of the 2,6-difluorobenzamide, 2-chloroacetaldehyde dimethyl acetal and concentrated sulfuric acid is 1:1.5: 15;

[0060] S2, providing intermediate 2, wherein, the preparation method of intermediate 2 is: add 0.03mol 3-tert-butylphenol, 0.09mol potassium carbonate and 35mL DM...

Embodiment 2

[0065] A synthetic method of etoxazole hapten, comprising the steps of:

[0066] S1, providing intermediate 1, wherein the preparation method of intermediate 1 is: add 2,6-difluorobenzamide and 2-chloroacetaldehyde dimethyl acetal to a one-necked bottle, and stir for 5 minutes under ice-water bath conditions , then slowly add concentrated sulfuric acid to it, after the dropwise addition, react overnight at room temperature, after the reaction, pour the reaction solution into ice water, stir well, extract 2-3 times with ethyl acetate, combine the organic phases, organic After washing and concentrating, the phase is purified by column to obtain intermediate 1; wherein, the ratio of the amount of substances of the 2,6-difluorobenzamide, 2-chloroacetaldehyde dimethylacetal and concentrated sulfuric acid is 1:1.2: 10;

[0067] S2, intermediate 2 is provided, wherein, the preparation method of intermediate 2 is: add 0.03mol 3-tert-butylphenol, 0.3mol potassium carbonate and 35mL DM...

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Abstract

The invention discloses an etoxazole hapten, and a synthesis method and an application thereof. The synthesis method comprises the following steps: synthesizing an intermediate 1 from 2,6-difluorobenzamide and 2-chloro-1,1-dimethoxyethane which are used as starting materials; reacting 3-tert-butyl phenol with a compound 1 under an alkaline condition to form an intermediate 2; reacting the intermediate 1 with the intermediate 2 to form an intermediate 3; carrying out an intramolecular condensation reaction on the intermediate 3 under the action of a strong alkali to form an intermediate 4; andoxidizing the intermediate 4 to form the final target. A linking arm is derivatized to the phenyl ether structure of etoxazole, the derivatized tether contains a carboxyl group, and the synthesized etoxazole hapten maximally reserves the characteristic structure of etoxazole, so the immunogenicity of the etoxazole hapten is obviously enhanced, and the etoxazole hapten also has the carboxyl group which can be coupled with a carrier; and immunization of an animal with an ethiazole artificial antigen obtained by coupling the etoxazole hapten with the carrier is in favor of stimulating the immuneresponse of the animal in order to generate an antibody with a strong specificity and a high sensitivity.

Description

technical field [0001] The invention relates to the technical field of food safety detection, in particular to an etoxazole hapten and its synthesis method and application. Background technique [0002] Etoxazole (Etoxazole) is a new type of acaricide discovered by Yazhou Chemical Industry Co., Ltd. of Japan and jointly developed with Sumitomo Chemical of Japan. It belongs to diphenyloxazoline derivatives and inhibits the embryogenesis of mite eggs and The molting process from larvae to adults is effective for eggs and larvae. Etoxazole mainly controls the main mites such as citrus spider mite, pear spider mite, two-spotted spider mite, Kanzawa spider mite and apple spider mite. This product is a systemic acaricide, effective against mite eggs, larvae, and nymphs, but ineffective against adults. The acaricidal activity is significantly higher than other acaricides, for example, the activity is about 100 times higher than that of hexythiazox. By inhibiting the biosynthesis...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/14G01N33/53
CPCC07D263/14G01N33/53
Inventor 付辉杨星星李细清王伟维杨林林曾文涛王西丽金虹张鑫曾楚怡
Owner SHENZHEN BIOEASY BIOTECHNOLOGY CO LTD
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