2-cyano-3-(2,2-difluoro-1,3-benzodiox-4-yl)acrylic acid compound and its preparation method

A technology of benzodioxine and compounds, which is applied in the field of organic synthesis, can solve problems such as low yield and/or purity, difficulty in solvent recovery and application, and inability to obtain intermediate products independently, so as to reduce production costs and solvent recovery loss effect

Active Publication Date: 2018-10-12
苏州敬咨达检测服务有限公司
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AI Technical Summary

Problems solved by technology

[0007] The object of the present invention is to overcome problems such as low yield and / or purity commonly existing in existing fludioxonil intermediate synthesis methods, difficulty in solvent recovery and mechanical application, and inability to obtain intermediate products independently, and to provide a method for preparing fludioxonil The method of the intermediate, which can obtain the fludioxonil intermediate product 2-cyano-3-(2,2-difluoro-1,3-benzodiox-4-yl) with higher yield and purity acrylic compound

Method used

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  • 2-cyano-3-(2,2-difluoro-1,3-benzodiox-4-yl)acrylic acid compound and its preparation method

Examples

Experimental program
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Effect test

Embodiment 1-14 and comparative example 1-3

[0044] Add 2,2-difluoro-1,3-benzodiox-4-aldehyde shown in formula (II) and cyanoacetic acid derivative shown in formula (III) in the four-neck flask with mechanical stirring, then Add solvent and stir to mix well. The temperature of the mixture was lowered to the reaction temperature and kept constant, then the catalyst was added dropwise with stirring, and the stirring was continued for a certain reaction time. After the reaction is completed, filter, recover the obtained filtrate and apply it mechanically, wash the obtained filter cake and dry the washed solid at 70° C. for 12 hours to obtain the final product.

[0045] Embodiment 1-14 and the used material of the reaction of comparative example 1,3 and consumption are shown in Table 1, and reaction condition is shown in Table 2; The material of comparative example 2 and reaction condition are according to Li Chao etc. Synthesis, Modern Pesticides, 2009, 8(3), 19-21, 24).

[0046] Table 1

[0047]

[0048] Table 2

[...

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Abstract

The invention relates to the field of organic synthesis and discloses a preparation method for 2-cyano-3-(2,2-difluoro-1,3-benzodioxyl-4-yl)acrylic compounds as shown in a formula I. The method comprises the following step: subjecting a compound as shown in a formula (II) and the compound as shown in a formula (III) to contact reaction in the presence of a catalyst, wherein the catalyst is an alkali nitrogen-contained organic compound; R1 is NHR2 or OR3; R2 is an alkyl group or an aromatic group of H and C1 to C6; and R3 is the alkyl group or the aromatic group of C1 to C6. With the method provided by the invention, fludioxonil intermediate products--the 2-cyano-3-(2,2-difluoro-1,3-benzodioxyl-4-yl)acrylic compounds with yield of more than 95% and purity of more than 99 wt% can be obtained.

Description

technical field [0001] The present invention relates to the field of organic synthesis, in particular to a method for preparing 2-cyano-3-(2,2-difluoro-1,3-benzodiox-4-yl)acrylic compounds, and the Methods Prepared 2-cyano-3-(2,2-difluoro-1,3-benzodiox-4-yl)acrylic acid compound. Background technique [0002] Fludioxonil is a new type of contact protection fungicide with a unique mechanism of action. It inhibits the growth of pathogenic mycelium by inhibiting the transfer related to glucose phosphorylation, and finally leads to the death of pathogenic bacteria. When applied to flowers, it mainly prevents diseases such as leaf blight, leaf spot, partial stem rot, and root rot. It is easy to use, can be used for foliar spraying and root irrigation, and has a small dosage and low residue; it has obvious effect on pathogenic bacteria that are resistant to other chemicals; it has no systemic effect, but has strong penetrating ability. It has a remarkable control effect on root ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D317/46
CPCC07D317/46
Inventor 吴浩王彦强杨海舰
Owner 苏州敬咨达检测服务有限公司
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