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Method for synthesizing chlorantraniliprole

A technology of chlorantraniliprole and synthetic method, applied in the field of organic synthesis, can solve problems such as low reaction yield and harsh reaction conditions, and achieve the effects of easy separation and purification, less by-products, and reduced production costs

Pending Publication Date: 2018-06-22
GUANGDONG MARUBI BIOLOGICAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] In order to overcome the shortcomings and shortcomings of harsh reaction conditions and low reaction yields in the prior art for preparing chlorantraniliprole, the purpose of the present invention is to provide a synthetic method for chlorantraniliprole

Method used

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  • Method for synthesizing chlorantraniliprole
  • Method for synthesizing chlorantraniliprole
  • Method for synthesizing chlorantraniliprole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Synthesis of S1.N-methyl-3-methyl-2-amino-benzamide (17)

[0050]

[0051] Take a 100mL three-necked flask, suspend 0.45g of 2-amino-3-methylbenzoic acid (16) in 30mL of distilled CH 2 Cl 2 In, add 0.4g HOBt (1-hydroxybenzotriazole). 0.84 g of 30% methylamine alcohol solution was added in an ice bath, and 0.86 g of EDCI was added with stirring in an ice bath. After the feeding was completed, the mixture was stirred and reacted in an ice bath for about 30 minutes. Then remove the ice bath, and leave overnight at room temperature. After the reaction, the obtained reaction was washed three times with 30 mL of water, dichloromethane was distilled off under reduced pressure to obtain a white solid, which was weighed to obtain 0.45 g after drying, with a yield of 90%.

[0052] Synthesis of S2.N-methyl-3-methyl-2-amino-5-chloro-benzamide (4)

[0053]

[0054] Take a 100mL three-necked flask, dissolve 0.45g of N-methyl-3-methyl-2-amino-benzamide (17) in 20mL of aceto...

Embodiment 2

[0056] S1. Synthesis of 3-amino-5-methylpyrazole (19)

[0057]

[0058] Put 2.46g of 3-aminocrotononitrile (18) and 20mL of 25% hydrazine hydrate mixture into a 50mL three-necked flask. Heat to reflux for reaction. After the reaction, excess hydrazine hydrate was vacuum-dried. After distillation of the residue, 1.9 g of 3-amino-5-methylpyrazole (19) were obtained, yield 65%.

[0059] S2. Synthesis of 3-methyl-5-bromopyrazole (20)

[0060]

[0061] Mix 1.9g of 3-amino-5-methylpyrazole (19), 15mL of concentrated hydrobromic acid, and 2.8g of cuprous bromide in a 100mL three-necked flask, and heat to 70°C. Dissolve about 1.5g of sodium nitrite in 5mL of water, and slowly drop it into a three-necked flask using a constant pressure funnel. After the addition was complete, the reaction solution was stirred at 70°C for 30 min, then cooled to room temperature, and 20 mL of THF (tetrahydrofuran) and 20 mL of water were added. It was extracted three times with 30 mL of diethy...

Embodiment 3

[0069] S1. Synthesis of Chlorantraniliprole (1)

[0070]

[0071] Dissolve 1 eq 1-(3-chloro-2-pyridyl)-3-bromo-1H-5-pyrazolecarboxylic acid (3-OH) in an appropriate amount of redistilled CH 2 Cl 2 In, add 1.3eq HOBt. 1eq N-methyl-3-methyl-2-amino-5-chloro-benzamide (4) was added in an ice bath, and 1.3eq EDCI was added with stirring in an ice bath. After the feeding was completed, the mixture was stirred and reacted in an ice bath for about 30 minutes. Then remove the ice bath, and leave overnight at room temperature. After the reaction, the obtained reaction was washed three times with 30 mL of water, and dichloromethane was distilled off under reduced pressure to obtain chlorantraniliprole. The yield was 91.5%.

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Abstract

The invention discloses a method for synthesizing chlorantraniliprole, and relates to the field of organic synthesis. The synthesis method of two key intermediates, 1-(3-chloro-2-pyridyl)-3-bromo-1H-5-pyrazole carboxylic acid and N-methyl-3-methyl-2-amino-5-chloro-benzamide is redesigned and improved, and finally the final product chlorantraniliprole is synthesized through an amidation reaction. According to method for synthesizing chlorantraniliprole, a route is provided for synthesis of the intermediate 1-(3-chloro-2-pyridyl)-3-bromo-1H-5-pyrazole carboxylic acid, and steps in the synthesismethod have mild reaction conditions and can obtain good yield, so that the problems of harsh reaction conditions and extremely low yield of key steps in the prior art are solved, and the production cost of chlorantraniliprole is reduced greatly; in the synthesis method, few by-products are produced in the steps, separation and purification are easy to implement, and further convenience is provided for industrial production.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a chlorantraniliprole (3-bromo-N-[4-chloro-2-methyl-6-[(methylcarbamoyl)benzene]-1-(3- Chloropyridin-2-yl)-1H-pyrazole-5-carboxamide) synthetic method. Background technique [0002] Chlorantraniliprole is the first broad-spectrum antibacterial agent discovered and developed by DuPont with a new chemical structure of o-amidobenzamides. Chlorantraniliprole’s ISO common name is Chlorantraniliprole, and its chemical name is 3-bromo-N-[4-chloro-2-methyl-6-[(methylcarbamoyl)benzene]-1-(3-chloropyridine -2-yl)-1H-pyrazole-5-carboxamide, CAS Registry No. 500008-45-7. Its chemical structural formula is as formula 1: [0003] [0004] The synthesis of chlorantraniliprole (1) mainly contains two methods at present: one is 5-methyl-7-chloro-2-[3-bromo-1-(3-chloro-2-pyridyl)- 1H-pyrazole]-4H-1,3-benzoxazin-4-one (2) undergoes a ring-opening reaction with methylamine; the other is N-met...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04C07C231/12C07C231/10C07C237/30
CPCC07C231/10C07C231/12C07D401/04C07C237/30
Inventor 孙平华傅裕航钱垂文孙怀庆裴运林聂艳凤
Owner GUANGDONG MARUBI BIOLOGICAL TECH CO LTD
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