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Synthesis method of chiral fenoxanil

A technology of blastamide and chirality, which is applied in the field of synthesis of pesticide compounds, can solve the problems of waste water, waste gas, high reaction cost, serious pollution, etc., and achieve high environmental protection benefits, simple synthesis route, and less waste gas.

Active Publication Date: 2017-02-01
JINGBO AGROCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

During the synthesis process, hydrolysis and chlorination steps are required, and a lot of waste water and waste gas are produced, resulting in high reaction costs and serious pollution.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] (S)-Preparation of ethyl p-toluenesulfonic acid lactate (compound I):

[0037] Throw 12g (0.1mol) of (S)-ethyl lactate (optical 98%), 19g (0.1mol) of p-toluenesulfonyl chloride, and 60g of toluene into the four-neck flask, stir at room temperature for 12 hours, and add 15g of triethylamine to the system (0.15mol), stirred and reacted for 2h, washed twice with water and then directly used in the next reaction.

[0038] (R) Preparation of ethyl 2-(2,4-dichlorophenoxy)propionate (compound II):

[0039] Add 16.3 g (0.1 mol) of 2,4-dichlorophenol, 70 g toluene, and 4.8 g (1.2 mol) of sodium hydroxide to the four-neck flask, add compound I (0.95 mol) obtained in the previous step to the system at 80 ° C, and raise the temperature Reflux at 110°C for 2 hours, wash twice with water, remove toluene from the organic phase under negative pressure to obtain ethyl (R)-2-(2,4-dichlorophenoxy)propionate with a normalized content of 95%, optical 97% .

[0040] Preparation of (R)-N-(...

Embodiment 2

[0043] (S)-Preparation of ethyl p-toluenesulfonic acid lactate (compound I):

[0044] Throw 12g (0.1mol) of (S)-ethyl lactate (optical 98%), 19g (0.1mol) of p-toluenesulfonyl chloride, and 60g of toluene into a four-necked flask, stir at room temperature for 12 hours, and add 11.9g of pyridine to the system ( 0.15mol), stirred and reacted for 2 hours, washed twice with water and then directly used in the next reaction.

[0045] (R) Preparation of ethyl 2-(2,4-dichlorophenoxy)propionate (compound II):

[0046] Add 16.3g (0.1mol) of 2,4-dichlorophenol, 70g toluene, and 16.8g (1.2mol) of potassium carbonate to the four-neck flask, add compound I (0.95mol) obtained in the previous step to the system at 80°C, and heat up to Reflux reaction at 110°C for 2 hours, wash twice with water, remove toluene from the organic phase under negative pressure to obtain ethyl (R)-2-(2,4-dichlorophenoxy)propionate with a normalized content of 96%, optical 96% .

[0047] Preparation of (R)-N-(1-c...

Embodiment 3

[0050] (S)-Preparation of ethyl methanesulfonic acid lactate (compound I):

[0051] Throw 12g (0.1mol) of (S)-ethyl lactate (optical 98%), 11.5g (0.1mol) of methanesulfonyl chloride, and 60g of toluene into the four-necked bottle, stir at room temperature for 8 hours, and add 15g of triethylamine to the system (0.15mol), stirred and reacted for 2h, washed twice with water and then directly used in the next reaction.

[0052]Preparation of (R)-2-(2,4-dichlorophenoxy) ethyl propionate (compound II):

[0053] Add 16.3g (0.1mol) of 2,4-dichlorophenol, 70g toluene, 16.8g (1.2mol) of potassium carbonate, and compound I (0.95mol) to a four-neck flask, heat up to 110°C for 2 hours under reflux, and wash twice with water , after the toluene is removed from the organic phase under negative pressure, (R)-2-(2,4-dichlorophenoxy) ethyl propionate with a normalized content of 95% is obtained, and the optical content is 96.5%.

[0054] Preparation of (R)-N-(1-cyano-1,2-dimethylpropyl)-2-(2...

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Abstract

The invention relates to a synthesis method of chiral fenoxanil. The synthesis method of the chiral fenoxanil is characterized in that chiral ethyl lactate is subjected to sulfonylation reaction to obtain sulfonic acid ester; the sulfonic acid ester reacts with 2,4-dichlorophenol to generate 2-(2,4-dichlorophenoxy) ethyl propionate; the 2-(2,4-dichlorophenoxy) ethyl propionate and 2,-amino-2,3-dimethyl nitrile are subjected to ammonia ester exchange reaction to generate corresponding chiral fenoxanil, wherein the molar ratio of the 2-(2,4-dichlorophenoxy) ethyl propionate to the 2,-amino-2,3-dimethyl nitrile is 1:1 and the reaction temperature is 60 to 85 DEG C. The method is simple in synthesis route, hydrolysis and chlorination are not needed, little waste water and waste gas are generated, a high environmentally-friendly benefit is achieved, the production cost is greatly reduced, the condition is mild, the fenoxanil with optical chirality can be synthesized in an oriented mode by selecting different configuration of ethyl lactate, and important significance of further exploring the optical property of the fenoxanil is achieved.

Description

technical field [0001] The invention relates to the technical field of pesticide compound synthesis, in particular to a method for synthesizing chiral blastamide. Background technique [0002] Rice blastamide, also known as cyanoprodil, is a phenoxyamide fungicide. Its mechanism of action is a black biosynthesis inhibitor, mainly inhibiting the activity of cylindroxone dehydrogenase, thereby inhibiting the formation of melanin by the blast fungus. It has good systemic absorption and excellent specific effect, and it also has a good effect on newly expanded leaves after application. [0003] At present, our research on the optical properties of blastamide is not deep enough, so the directional synthesis of chiral blastamide is helpful for further research on the optical properties of blastamide. [0004] The present invention provides a method for synthesizing (R)-N-(1-cyano-1,2-dimethylpropyl)-2-(2,4-dichlorobenzene) with (S)-ethyl lactate as raw material Oxygen) propionam...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/30C07C255/29
CPCC07B2200/07C07C67/31C07C253/30C07C303/28C07C255/29C07C69/712C07C309/73
Inventor 葛红丹戴荣华韦能春成道泉王建刚曹同波
Owner JINGBO AGROCHEM TECH CO LTD
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