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Method for preparing flumioxazin

A technology of propargyl and propargyl, which is applied in the field of preparing propargyl, can solve the problems of low purity and high organic impurities, and achieves the effects of simple method and easy industrialization.

Active Publication Date: 2015-11-18
苏州敬咨达检测服务有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The purpose of the present invention is to overcome the problem that the product yield and / or purity are not high and the organic impurities are usually high when the prior art is used for the preparation of flumechlor, and a method for preparing flumecil is provided.

Method used

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  • Method for preparing flumioxazin
  • Method for preparing flumioxazin
  • Method for preparing flumioxazin

Examples

Experimental program
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Effect test

Embodiment 1

[0054] Take 20g of 99% 6-amino-7-fluoro-4-propynyl-1,4-benzoxazin-3(4H)-one, 100mL of 1,2-dichloroethane, 1.05 equivalents of 99.5% content of 3,4,5,6-tetrahydrophthalic anhydride, 1.4mL acetic acid and 1mL piperidine were placed in a reaction flask, refluxed for 7 hours for azeotropic dehydration, after the reaction was completed, water was added to azeotropically remove 1,2-dichloroethane alkanes, filtered, and the resulting filter cake was beaten with 95% ethanol, filtered, and dried to obtain flumecil propargyl, with a yield of 96.2%, a purity of 99.5%, and an organic impurity content of 0.09% by weight.

[0055] The resulting product is detected by nuclear magnetic resonance with BRUKERAVANCE500 equipment, and the obtained nuclear magnetic resonance spectrum is shown in Figure 1a shown, and organize the data in the map as Figure 1b ;From Figure 1a and Figure 1b It can be seen from the figure that the number of hydrogens on the nuclear magnetic map, the chemical shift...

Embodiment 2

[0057] Take 20 g of 99% 6-amino-7-fluoro-4-propynyl-1,4-benzoxazin-3(4H)-one and 80 mL of toluene, 1.1 equivalents of 99.5% 3,4, 5,6-tetrahydrophthalic anhydride, 1.4mL acetic acid and 1.2mL piperidine were placed in a reaction flask, and refluxed for 6 hours for azeotropic dehydration. After the reaction was completed, water was added to remove toluene azeotropically, filtered, and the obtained filter cake was washed with 95% ethanol Slurry, filter and dry to obtain flumecil propargyl, with a yield of 90.5%, a purity of 99.3% by weight, and an organic impurity content of 0.1% by weight. .

Embodiment 3

[0059]Take 20g of 6-amino-7-fluoro-4-propynyl-1,4-benzoxazin-3(4H)-one with a content of 99% and 120mL of methyl isobutyl ketone (MIBK), 1.05 equivalents of 99.5 % content of 3,4,5,6-tetrahydrophthalic anhydride, 1.4mL trifluoroacetic acid and 1.5mL piperidine were placed in a reaction flask, and refluxed for 8 hours for azeotropic dehydration. Butyl ketone (MIBK), filtered, beating with 95% ethanol, filtered, and dried to obtain flumecil propargyl, with a yield of 90.0%, a purity of 99.1% by weight, and an organic impurity content of 0.1% by weight.

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Abstract

The invention relates to the field of organic synthesis, and discloses a method for preparing flumioxazin. The flumioxazin has a structure shown in the formula (I) (in the description). The method is characterized by comprising the following steps: under the existence of a catalyst, enabling 6-amino-7-fluoro-4-propinyl-1, 4-benzoxazin-3(4H)-one shown in the formula (II) (in the description) and 3, 4, 5, 6-Tetrahydrophthalic anhydride shown in the formula (III) (in the description) to be subjected to contact reaction in a solvent, wherein the catalyst is an alkaline nitric organic matter or a mixture of organic acid and the alkaline nitric organic matter. The flumioxazin product prepared by the method has the advantages that the yield can reach 90% or above, the purity can reach 99 wt% or above, and the content of organic impurities can be smaller than 0.1 wt%; the method is simple, and easy for industrialization.

Description

technical field [0001] The present invention relates to the field of organic synthesis, in particular to a method for preparing flufenazim. Background technique [0002] Propyrylflufen (often referred to as "quick harvest") is an N-phenylphthalimide herbicide absorbed by young shoots and leaves created and developed by Japan's Sumitomo Chemical Industry Co., Ltd. for soil treatment It can effectively control annual broad-leaved weeds and some grass weeds, is easy to degrade in the environment, and is safe for subsequent crops. Soybeans and peanuts have good resistance to it, and corn, wheat, barley, and rice have moderate tolerance. Therefore, this herbicide is widely used in agricultural production and has huge economic market value. [0003] There are many synthetic methods for the synthesis of flurafen propargyl, such as: [0004] US4640707 discloses a method for the preparation of fluflumecil propargyl, specifically including (Example 1): 6-amino-4-(2-propynyl)-2H-1,4-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/04
CPCC07D413/04
Inventor 吴浩黄广英王彦强李鼎盛王凯杨海舰
Owner 苏州敬咨达检测服务有限公司
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