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Method for synthesizing clethodim

A technology for clethodim and ketene, applied in the field of pesticide synthesis, can solve the problems of low overall yield of clethodim, small pH value range, difficult production and operation, etc., and achieves low production cost, good product quality, and little environmental pollution. Effect

Inactive Publication Date: 2017-09-15
江苏威格瑞斯化工有限公司
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  • Abstract
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  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The disadvantage of this method is that the suitable pH range of the condensation reaction after hydrolysis is small, it is not easy to produce and operate, and the overall yield of clethodim is low

Method used

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  • Method for synthesizing clethodim
  • Method for synthesizing clethodim
  • Method for synthesizing clethodim

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preparation example Construction

[0059] D. The preparation method of clethodim

[0060] Reaction of (±)-2-[propionyl]-3-[hydroxyl]-5-[2-(ethylthio)propyl]cyclohex-2-enone with chloroallyloxyamine to prepare clethod Ketones (Formula I):

[0061]

[0062] in:

[0063] The reaction temperature of intermediate VIII and chloroallyloxyamine is 10-50°C, more preferably 20-30°C; the reaction time is 1-5h, more preferably 2-3h. If the temperature is too high and the time is too long, impurities will increase; if the temperature is too low and the time is too short, the reaction will be incomplete.

[0064] In a specific embodiment of the present invention, its reaction process is as follows:

[0065]

specific Embodiment

[0069] 1) Preparation of 6-ethylthio-3-hepten-2-one (formula III):

[0070] Add 100g (purity 97.8%, 0.888mol) of 3,5-heptadiene-2-one (formula II), 2.76g (0.027mol) triethylamine into the reaction flask, stir at room temperature (20-25°C) for 15 Minutes later, the temperature was slowly raised to 55°C, and 60.69g (0.977mol) of ethanethiol was started to be added dropwise. The temperature of the dropping process was controlled at 55-65°C. Gas chromatography traced the complete reaction (3,5-heptadien-2-one ≤ 1%), lowered to room temperature (20-25°C), added 400ml of water and 1000ml of toluene, stirred for 30 minutes, stood still for 30 minutes, and separated; Add 100ml of 0.5% dilute hydrochloric acid to the organic layer, stir and wash, and let stand for liquid separation; add 200ml of water to the organic layer and stir for 30 minutes, let stand for 30 minutes, and separate the liquids. When moisture≤0.1%, stop water separation and cool to room temperature, obtain 1011g of ...

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Abstract

The present invention proposes a method for synthesizing clethodim, comprising 3,5-heptadiene-2-one (formula II) and ethanethiol for nucleophilic addition to prepare clethodim intermediate 6-ethylthio ‑3‑heptene‑2‑ketone (formula III); formula III reacts with dimethyl malonate and propionyl chloride to prepare (±)‑3‑[propionyloxy]‑5‑[ 2-(Ethylthio)propyl]-6-[methoxyformyl]cyclohex-2-enone (Formula V); Formula V is then rearranged, hydrolyzed and decarboxylated to obtain (±)-2- [Propionyl]-3-[hydroxyl]-5-[2-(ethylthio) propyl]cyclohex-2-enone (formula VIII); formula VIII reacts with chloroallyloxyamine to obtain alkene Clethodim (formula I), the method for preparing clethodim by using intermediate 3,5-heptadiene-2-one (formula II) in the present invention is proposed for the first time, and the clethodim (formula I) prepared by this method is generally The yield is high, the product quality is good, and the method has low production cost and little environmental pollution, and is suitable for large-scale production.

Description

technical field [0001] The invention relates to the technical field of pesticide synthesis, in particular to a method for synthesizing clethodim. Background technique [0002] Clethodim is a cyclohexenone herbicide product developed by American Chevron Chemical Company in 1987. Clethodim is a foliage herbicide. It is an efficient, safe and highly selective ACCase inhibitor. It has special effects on most annual and perennial grass weeds and is safe to dicotyledonous crops. [0003] The chemical name of clethodim is (±)-2-[(E)-3-chloroallyloxyimino]propyl-5-[2-(ethylthio)propyl]-3-hydroxycyclohexyl -2-enone, its chemical structural formula is as follows: [0004] [0005] There are two main synthetic routes of clethodim at the present stage: [0006] Route 1: Synthesize clethodim by witting reaction, the process route is as follows: [0007] [0008] The above-mentioned method of witting reagent has high cost, difficult post-treatment, and relatively large pollution...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/20C07C323/47
CPCC07C319/20C07C319/18C07C323/47C07C323/22C07C323/55
Inventor 缪汉东王威
Owner 江苏威格瑞斯化工有限公司
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