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Carfentrazone-ethyl synthesis method

A synthetic method and technology of metofen, which is applied in the field of chemistry and can solve problems such as complicated operation

Inactive Publication Date: 2013-12-18
NANJING UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] In 2011, Qunzhen Guo et al. invented a patent (CN102174026C, WO2012122863), using 1-(5-amino-2-fluoro-4-chlorophenyl)-3-methyl-4-difluoromethyl-1H-1 , 2,4-triazolin-5-one as a raw material, the target product is synthesized by diazoalkylation and esterification in two steps, and the operation is complicated

Method used

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  • Carfentrazone-ethyl synthesis method

Examples

Experimental program
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Effect test

Embodiment 1

[0018] Add acetonitrile (32.4g, 790mmol) in 250mL there-necked flask, logical N 2 , cooled to -5-0°C, add 1-(5-amino-2-fluoro-4-chlorophenyl)-3-methyl-4-difluoromethyl-1H-1,2,4-triazole Lin-5-ketone (10.5g, 35.9mmol) and cuprous chloride (2.50g, 25.1mmol), add concentrated hydrochloric acid (11.8g, 120mmol) dropwise while stirring, after 20min, add ethyl acrylate ( 49.4g, 494mmol), and then controlled the temperature at 0-5°C, added dropwise tert-butyl nitrite (5.6g, 53.9mmol), added 2.5h, stirred for 1h, recovered the solvent and unreacted ethyl acrylate by atmospheric distillation Esters were diluted with ethyl acetate, and cuprous chloride was recovered by filtration. Finally, impurities were evaporated under conditions of temperature 110-125° C. and pressure 15-20 mmHg to obtain 15.2 g of the product mefentrazone, with a yield of 103%. The content is 91.8%.

Embodiment 2

[0020] Add acetonitrile (32.4g, 790mmol) in 250mL there-necked flask, logical N 2 , cooled to -5-0°C, add 1-(5-amino-2-fluoro-4-chlorophenyl)-3-methyl-4-difluoromethyl-1H-1,2,4-triazole Lin-5-ketone (10.5g, 35.9mmol) and cuprous chloride (2.50g, 25.1mmol), add concentrated hydrochloric acid (11.8g, 120mmol) dropwise while stirring, after 20min, add ethyl acrylate ( 49.4g, 494mmol), and then controlled the temperature at 0-5°C, added dropwise tert-butyl nitrite (5.6g, 53.9mmol), added 2h, stirred for 1h, recovered the solvent and unreacted ethyl acrylate by atmospheric distillation , then dilute with ethyl acetate, filter and recover cuprous chloride, and finally evaporate impurities at a temperature of 110-125°C and a pressure of 15-20mmHg to obtain 14.7g of the product mefentrazone, with a yield of 99.3%. 92.0%.

Embodiment 3

[0022] Add acetonitrile (32.4g, 790mmol) in 250mL there-necked flask, logical N 2 , cooled to -5-0°C, add 1-(5-amino-2-fluoro-4-chlorophenyl)-3-methyl-4-difluoromethyl-1H-1,2,4-triazole Lin-5-ketone (10.5g, 35.9mmol) and cuprous chloride (2.50g, 25.1mmol), add concentrated hydrochloric acid (11.8g, 120mmol) dropwise while stirring, after 20min, add ethyl acrylate ( 49.4g, 494mmol), and then control the temperature at 0-5°C, dropwise add tert-butyl nitrite (5.6g, 53.9mmol), add 3.5h, stir for 1h, recover the solvent and unreacted ethyl acrylate by atmospheric distillation Esters were diluted with ethyl acetate, and cuprous chloride was recovered by filtration. Finally, the impurity was evaporated at a temperature of 110-125° C. and a pressure of 15-20 mmHg to obtain 15.5 g of the product mefentrazone, with a yield of 105%. The content is 91.8%.

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Abstract

The invention belongs to the technical field of pesticide herbicide, and particularly relates to a preparation method of a triazolinone herbicide carfentrazone-ethyl. The method is implemented mainly by a one-pot process, wherein 1-(5-amino-2-fluoro-4-chlorphenyl)-3-methyl-4-difluoromethyl-1H-1,2,4-triazoline-5-ketone is used as a raw material, acetonitrile or butanone is used as a solvent, tert-butyl nitrite is used as a diazotization reagent, and the compound carfentrazone-ethyl is synthesized by a one-pot process through diazotization and Meerwein reaction under the catalysis of cuprous chloride. The method provided by the invention has the advantages of high selectivity, mild reaction conditions, short reaction time, high product yield, environmental friendliness, easy implementation of industrialization and the like.

Description

technical field [0001] The invention belongs to the synthesis of organic compounds in the field of chemistry. In particular, it relates to a preparation method of mefentrazone. technical background [0002] The herbicide mefentrazone (also known as mefentrazone-ethyl, funon, mefenoxine), molecular formula: C 15 h 14 o 3 N 3 f 3 C1 2 , its structural formula is as follows: [0003] [0004] In 1990, Kathleen M. Poss et al. of FMC Company reported for the first time that phenyltriazolinones, including fentrazone, were synthesized by using tert-butyl nitrite as a diazotization reagent, copper chloride as a catalyst, and acetonitrile as a solvent. herbicide, and tested its activity, applied for the U.S., China and world patents (WO1990002120, CN1041154, US5125958), protected the structure of this series of compounds, and determined that the herbicide mefentrazone has a higher Herbicidal activity, which belongs to protoporphyrinogen oxidase inhibitor, that is, by inhib...

Claims

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Application Information

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IPC IPC(8): C07D249/12
Inventor 朱红军俞娟樊俭俭韩邦友何广科陈凯徐守林付行花邹爱宗徐超航
Owner NANJING UNIV OF TECH
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