Preparation method of chlorantraniliprole

A technology of chlorantraniliprole and methanol, which is applied in the field of preparation of chlorantraniliprole, can solve the problems that the production process is not easy to control, is not suitable for industrial production, and harsh reaction conditions, so as to achieve suitable industrial development and easy industrialization The effect of easy production and post-processing

Inactive Publication Date: 2019-12-27
ABA CHEM NANTONG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Aiming at the deficiencies of the prior art, the present invention provides a preparation method of chlorantraniliprole, which has the advantages of simple and convenient production, and solves the problem of harsh reaction conditions in the preparation process of chlorantraniliprole, and the equipment that needs to be used It is relatively complicated, the process of production process is not easy to control, and it is not suitable for industrial production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] The invention provides the following technical scheme: a preparation method of chlorantraniliprole, comprising the following steps:

[0030] 1) Add 4 parts of maleic anhydride and 4 parts of methanol into a single-necked bottle, stir and raise the temperature to 50°C and keep it warm for 0.5h to prepare monomethyl maleate;

[0031] 2) Cool 80 parts of hydrogen bromide-glacial acetic acid solution to 0°C, then dropwise add 3 parts of monomethyl maleate, keep stirring after adding, a large amount of yellow viscous substance will appear after 3 minutes, and 3-bromomaleic acid can be obtained monomethyl ester;

[0032] 3) Dissolve monomethyl 3-bromomaleate in 10 parts of dichloromethane, then add 4 drops of DMF dropwise, and add 2 parts of thionyl chloride dissolved in dichloromethane solution dropwise within 10 minutes to obtain 3-bromo Monomethyl maleate chloride;

[0033] 4) Add 18 parts of 2,3-dichloropyridine and 26 parts of ethylene glycol into a single-necked bottl...

Embodiment 2

[0042] The invention provides the following technical scheme: a preparation method of chlorantraniliprole, comprising the following steps:

[0043] 1) Add 6 parts of maleic anhydride and 6 parts of methanol into a single-neck bottle, stir and raise the temperature to 50°C and keep it warm for 1 hour to prepare monomethyl maleate;

[0044] 2) Cool down 100 parts of hydrogen bromide-glacial acetic acid solution to 0°C, add 4 parts of monomethyl maleate dropwise, keep stirring after adding, a large amount of yellow viscous substance will appear after 3-7 minutes, and 3-bromomaleic acid can be obtained. monomethyl torate;

[0045] 3) Dissolve 3-bromomonomethyl maleate in 13 parts of dichloromethane, then add 5 drops of DMF dropwise, and add 3 parts of thionyl chloride dissolved in dichloromethane solution dropwise within 15 minutes to obtain 3-bromo Monomethyl maleate chloride;

[0046] 4) Add 21 parts of 2,3-dichloropyridine and 28 parts of ethylene glycol into a single-necked ...

Embodiment 3

[0055] The invention provides the following technical scheme: a preparation method of chlorantraniliprole, comprising the following steps:

[0056] 1) Add 8 parts of maleic anhydride and 8 parts of methanol into a single-necked bottle, stir and raise the temperature to 50°C and keep it warm for 1.5h to prepare monomethyl maleate;

[0057] 2) Cool 120 parts of hydrogen bromide-glacial acetic acid solution to 0°C, add 5 parts of monomethyl maleate dropwise, keep stirring after adding, a large amount of yellow viscous substance will appear after 7 minutes, and 3-bromomaleic acid can be obtained monomethyl ester;

[0058] 3) Dissolve 3-bromomonomethyl maleate in 15 parts of dichloromethane, then add 6 drops of DMF dropwise, and add 4 parts of thionyl chloride dissolved in dichloromethane solution dropwise within 20 minutes to obtain 3-bromo Monomethyl maleate chloride;

[0059] 4) Add 24 parts of 2,3-dichloropyridine and 30 parts of ethylene glycol into a single-necked bottle to...

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PUM

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Abstract

The invention relates to the technical field of synthesis processes of insecticides, and discloses a preparation method of chlorantraniliprole, which comprises the following steps: 1) adding 4-8 partsof maleic anhydride and 4-8 parts of methanol into a single-necked bottle, stirring the mixture, heating to 50 DEG C, and carrying out heat preservation reaction for 0.5-1.5 hours to obtain monomethyl maleate; and 2) cooling 80-120 parts of a hydrogen bromide-glacial acetic acid solution to 0 DEG C, then dropwise adding 3-5 parts of the monomethyl maleate, after addition is completed, carrying out heat preservation and stirring for 3-7 min, so that a large amount of a yellow viscous substance appears, and the monomethyl 3-bromomaleate can be prepared. The invention discloses a preparation method of chlorantraniliprole. The maleic anhydride, 2,3-dichloropyridine and 2-amino-3-methylbenzoic acid are adopted as starting materials to synthesize the target compound chlorantraniliprole througha convergent reaction. The structure is determined through HNMR, the route is mild in reaction condition, easy and convenient to operate and separate, raw materials are easy to obtain, special equipment is not needed, industrial production is easy to achieve, the action mechanism is novel and unique, and wide application and development prospects are achieved.

Description

technical field [0001] The invention relates to the technical field of a synthesis process of an insecticide, in particular to a preparation method of chlorantraniliprole. Background technique [0002] Chlorantraniliprole, whose trade name is Kangkuan in China, is a new type of high-efficiency and low-toxic o-formamidobenzamide insecticide developed by DuPont Company of the United States. Insecticidal activity, has special effects on Lepidoptera insects, the chemical name is 3-bromo-N-{4-chloro-2-methyl-6-[(methylamino)carbonyl]phenyl}-1-(3-chloro -2-pyridyl)-1H-pyridine-5-amide. [0003] For example, a preparation method of chlorantraniliprole disclosed in Chinese patent CN 103058993 B, in the synthesis process of p-methylindole-2,3-dione, the preparation solution needs to be heated to 80°C and stirred for 10 minutes , stop the reaction, cool at room temperature, pour the reaction solution on crushed ice under stirring, let it stand overnight, and filter it with suction. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04
CPCC07D401/04
Inventor 蒋信义刘汝章徐军张敏华
Owner ABA CHEM NANTONG
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