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Method for transforming N-cyanomethyl bis(trifluoromethyl) nicotinamide into flonicamide and application thereof

A technology of trifluoromethyl nicotinyl and flonicamid, which is applied in the preparation of pesticides, and converts N-cyanomethyl bis(trifluoromethyl) nicotinamide into flonicamid, which can solve the difficulty of product purification, The problem of high impurity content

Active Publication Date: 2017-12-01
HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the prior art, the synthesis of flonicamid mainly takes 4-trifluoromethylnicotinic acid as the starting material, and directly reacts with aminoacetonitrile sulfate to prepare flonicamid after acyl chloride, and the yield is 43.5%; Impurities are easy to be produced during the production process of this method, because the content of impurities is high, and product purification is difficult

Method used

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  • Method for transforming N-cyanomethyl bis(trifluoromethyl) nicotinamide into flonicamide and application thereof
  • Method for transforming N-cyanomethyl bis(trifluoromethyl) nicotinamide into flonicamide and application thereof
  • Method for transforming N-cyanomethyl bis(trifluoromethyl) nicotinamide into flonicamide and application thereof

Examples

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Effect test

Embodiment １

[0060] Example 1 A method for converting N-cyanomethylbis(trifluoromethyl)nicotinamide into flonicamid

[0061] A method for converting N-cyanomethylbis(trifluoromethyl)nicotinamide into flonicamid, the synthetic route of which is:

[0062] ;

[0063] Wherein, the transformation reagent is an alkaline aqueous solution, an alkaline alcohol solution or an alkaline alcohol-water mixture;

[0064] The R is -H, -CH 3 、-C 2 h 5 One of them, if higher alcohols are used, the conversion rate will decrease.

[0065] The conversion reagent is an aqueous solution of triethylamine, an alcoholic solution of triethylamine or an alcohol-water mixture of triethylamine;

[0066] Or an aqueous solution of pyridine, an alcohol solution of pyridine or a mixture of alcohol and water of pyridine;

[0067] Or NaOH aqueous solution, NaOH alcohol solution or NaOH alcohol water mixture;

[0068]

[0069] 1) When the conversion reagent is an aqueous solution of triethylamine, the specific con...

Embodiment 2

[0080] Example 2 Application of a method for converting N-cyanomethylbis(trifluoromethyl)nicotinamide into flonicamid

[0081] An application of a method for converting N-cyanomethylbis(trifluoromethyl)nicotinamide into flonicamid, the synthetic route of which is:

[0082] ;

[0083] Wherein, the transformation reagent is an alkaline aqueous solution, an alkaline alcohol solution or an alkaline alcohol-water mixture;

[0084] The R is -H, -CH 3 、-C 2 h 5 One of.

[0085] The conversion reagent is an aqueous solution of triethylamine, an alcohol solution of triethylamine or a mixed solution of alcohol and water of triethylamine.

[0086] 1) When the conversion reagent is an aqueous solution of triethylamine, its preparation method is:

[0087] Dissolve 4-trifluoromethylnicotinoyl chloride in tetrahydrofuran solution, add triethylamine and aminoacetonitrile hydrochloride; react at a temperature of 30-50 °C for 10 h, then add water to quench the reaction, extract with eth...

Embodiment 3-7

[0111] Example 3-7 The method of converting N-cyanomethylbis(trifluoromethyl)nicotinamide into flonicamid

[0112] Examples 3-7 are respectively a method for converting N-cyanomethylbis(trifluoromethyl)nicotinamide into flonicamid, which is similar to the preparation method described in Example 1, except that The technical parameters involved are different, as shown in the following table:

[0113]

[0114]

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Abstract

The invention discloses a method for transforming N-cyanomethyl bis(trifluoromethyl) nicotinamide into flonicamide. A transforming reagent is adopted, so that transformation rate of transforming the N-cyanomethyl bis(trifluoromethyl) nicotinamide into the flonicamide is 98.1-99.8%, and purity is 97.1-99.5%. The invention also provides application of the method for transforming the N-cyanomethyl bis(trifluoromethyl) nicotinamide into the flonicamide, not only impurities can be transformed into the flonicamide with pharmaceutical value, but also the impurities produced in a transformation process can be recycled, so that the final yield of the flonicamide is 69.59-75.83%, and the method is more applicable to industrial production. The method disclosed by the invention is applicable to preparation of the flonicamide.

Description

technical field [0001] The invention belongs to the field of pharmacy and relates to a method for preparing pesticides, in particular to a method and application for converting N-cyanomethylbis(trifluoromethyl)nicotinamide into flonicamid. Background technique [0002] Flonicamid (Flonicamid, developed by Ishihara Sangyo Co., Ltd., Japan) is a low-toxicity pyridinamide (or nicotinamide) insect growth regulator insecticide. As a high-efficiency selective insecticide, flonicamid has strong penetration , long-lasting effect and good systemic properties, and has a novel mechanism of action, which can make piercing-sucking mouthpart pests such as aphids quickly resist food, and has good neurotoxicity. Due to its low toxicity to bees, its application prospect is broad. [0003] In the prior art, the synthesis of flonicamid mainly takes 4-trifluoromethylnicotinic acid as the starting material, and directly reacts with aminoacetonitrile sulfate to prepare flonicamid after acyl chlo...

Claims

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Application Information

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IPC IPC(8): C07D213/82C07D213/80C07D213/803
CPCC07D213/80C07D213/803C07D213/82
Inventor 董新蕊束学野王迎楠郭庆春张越冯雪
Owner HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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