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Method for synthesizing carfentrazone-ethyl

A technology of caroxafen-ethyl and phenyltriazolinone is applied in the field of chemistry, and can solve the problems of complicated substitution and elimination reaction operation steps, unfavorable industrial production, and difficulty in obtaining 2-isohydroxyethyl ethyl acrylate, and achieves the following advantages. Conducive to industrialized production, optimized synthesis method and shortened reaction time

Inactive Publication Date: 2018-04-20
HUAIAN GUORUI CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The raw material 2-isohydroxyethyl acrylate required for the synthetic method disclosed in the above patent is not easy to obtain, and the replacement and elimination reaction operation steps are complicated, which is not conducive to industrial production

Method used

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  • Method for synthesizing carfentrazone-ethyl
  • Method for synthesizing carfentrazone-ethyl
  • Method for synthesizing carfentrazone-ethyl

Examples

Experimental program
Comparison scheme
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Embodiment 1

[0038] Example 1. Add 4-chloro-2-fluorophenylhydrazine and trimethyl orthoformate to methanol as a solvent, add triethylamine dropwise, heat to reflux, and detect the reaction by TLC until the reaction is complete. Put the above reaction solution in an ice-water bath On, then potassium cyanate was added, acetic acid was added dropwise, and then the catalyst (ureapropionic acid) was added and stirred until the reaction was complete.

[0039]

[0040] Raw material addition

[0041]

[0042] Effect of catalyst on reaction time and yield

[0043]

[0044] In the case of adding a catalyst, potassium cyanate and sodium cyanate are selected

[0045]

[0046] With the addition of a catalyst, phenylhydrazine and trimethyl orthoformate

[0047]

[0048] Product NMR data: 1 HNMR (400MHz, CDCl 3 , δppm): 2.48(s, 3H), 6.26(s, 1H), 7.02(t, J=58.0Hz, 1H), 7.35(d, J=9.6Hz, 1H), 7.97(d, J=7.8Hz , 1H).

Embodiment 2

[0049] Example 2. The raw material phenyl-substituted triazolinone (6.9 g, 0.03 mol) was weighed in a 250 mL three-neck flask, and 50 mL of DMF was added to stir to dissolve it. The system temperature was heated to reflux, and potassium carbonate (6.90 g, 0.05 mol) was added. Continue to stir, the system turns into wine red, pass through chlorodifluoromethane gas, TLC traces the reaction after 20min, the obtained mixture is extracted twice with ethyl acetate, the organic layer is mixed, dried over anhydrous magnesium sulfate, filtered, and concentrated to obtain a white solid compound III, 6.64g, yield 80%. 1 HNMR (400MHz, CDCl 3 , δppm): 2.48(s, 3H), 7.26(s, 1H), 7.02(t, J=58.0Hz, 1H), 7.35(d, J=9.6Hz, 1H), 7.97(d, J=7.8Hz , 1H).

Embodiment 3

[0050] Example 3: Fluorinated triazolinone (13.9 g, 0.05 mol), concentrated sulfuric acid was added into an ice-salt bath, stirred until all solids were dissolved, and then iodine powder (12.7 g, 0.05 mol) was added. The mixture was then warmed to room temperature and stirred (reaction monitored by TLC). The reaction mixture was poured into 300 g of ice, and the obtained mixture was extracted twice with dichloromethane, the organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated to obtain 18.33 g of compound IV as a white solid, with a yield of 91%. 1 HNMR (400MHz, CDCl 3 , δppm): 2.46 (s, 3H), 7.02 (t, J=58.0Hz, 1H), 7.35 (d, J=9.8Hz, 1H), 7.97 (d, J=7.6Hz, 1H).

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Abstract

The invention relates to a method for synthesizing carfentrazone-ethyl. According to the method, synthesis of a phenyltriazolinone intermediate is optimized, reaction time is shortened, and reaction yield is increased. The invention provides a synthetic method for better optimizing the phenyltriazolinone intermediate. Besides, the method disclosed by the invention has the advantages that the stepsof preparing the carfentrazone-ethyl are optimized, raw materials which are obtained more easily are selected, and industrial production is facilitated.

Description

technical field [0001] The invention belongs to the synthesis of organic compounds in the field of chemistry, in particular to a method for synthesizing pyrentrazone-ethyl. Background technique [0002] The chemical name of the herbicide mefentrazone-methyl (also known as mefentrazone, mefentrazone-ethyl, triafentrazone-ethyl, funon, mefenoxate) is 2-chloro-3-[2-chloro-5-(4- Difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)-4-fluorophenyl]propionic acid ethyl ester, its chemical The structure is as follows: [0003] [0004] Mefentrazone-ethyl belongs to triazolinone herbicides. It is an important class of herbicides. It has a very broad application prospect because of its characteristics of low dosage, fast weeding, wide herbicidal spectrum and not easy to produce resistance. Mefentrazone-ethyl inhibits protoporphyrinogen oxidase in the process of chlorophyll biosynthesis to cause cell membrane damage, causing leaves to dry up and die quickly. The herbi...

Claims

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Application Information

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IPC IPC(8): C07D249/12
CPCC07D249/12
Inventor 张胜王玉池陈文毛更生陈明光张璞
Owner HUAIAN GUORUI CHEM CO LTD
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