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A kind of method for preparing n-acyl anthranilamide

A technology of aminobenzamide and acyl group, applied in the field of organic synthesis, can solve the problems of difficult treatment of sulfur-containing organic acid wastewater, unfavorable industrial production, low yield, etc., to avoid the problem of sulfur-containing organic acid wastewater, convenient operation, The effect of high yield

Active Publication Date: 2020-06-16
MAX RUDONG CHEM
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Problems solved by technology

[0011] Although this method has fewer steps than method one and method two, excessive methanesulfonyl chloride will be used, which will produce a large amount of sulfur-containing organic acid waste water which is difficult to handle, and the three wastes are serious, and the method yield is very low (two-step total yield rate is about 20%), which is not conducive to industrial production

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  • A kind of method for preparing n-acyl anthranilamide
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  • A kind of method for preparing n-acyl anthranilamide

Examples

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Embodiment 1

[0028] Example 1: 3-bromo-N-(2-methyl-4-chloro-6-(carbamoyl)phenyl)-1-(3-chloro-2-pyridyl)-1H-pyrazole-5 - Preparation of formamide (chlorantraniliprole)

[0029] Step 1: In a 100mL three-necked flask, add 3.02g of 3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxylic acid, 1.95g of 3-picoline and 15mL of acetonitrile , POBr was added dropwise at -5°C 3 5.73g, keep stirring for half an hour after dropping, then add 1.86g of 2-amino-3-methyl-5-chlorobenzoic acid, and react at room temperature for 1 hour. Add 20 mL of water and stir for 0.5 hours, filter, wash the filter cake with 3:2 acetonitrile-water, and dry to obtain 2-[3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5- Base]-6-chloro-8-methyl-4H-3,1-benzoxazin-4-one 4.16g, yield 92%.

[0030] The second step: the 2-[3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazol-5-yl]-6-chloro-8-methyl-4H obtained in the first step 4.16g of -3,1-benzoxazin-4-one was dissolved in 20ml of acetonitrile, then 0.92g of methylamine hydrochloride was...

Embodiment 2

[0031] Example 2: 3-bromo-N-(2-methyl-4-chloro-6-(carbamoyl)phenyl)-1-(3-chloro-2-pyridyl)-1H-pyrazole-5 - Preparation of formamide (chlorantraniliprole)

[0032] Step 1: In a 100mL three-necked flask, add 3.02g of 3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxylic acid, 1.95g of 3-picoline and 15mL of acetonitrile , POBr was added dropwise at -5°C 3 5.73g, keep stirring for half an hour after dropping, then add 1.86g of 2-amino-3-methyl-5-chlorobenzoic acid, and react at room temperature for 1 hour. Add 20 mL of water and stir for 0.5 hours, filter, wash the filter cake with 3:2 acetonitrile-water, and dry to obtain 2-[3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5- Base]-6-chloro-8-methyl-4H-3,1-benzoxazin-4-one 4.16g, yield 92%.

[0033] The second step: the 2-[3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazol-5-yl]-6-chloro-8-methyl-4H obtained in the first step 4.16 g of -3,1-benzoxazin-4-one was dissolved in 20 ml of acetonitrile, then 1.11 g of triethylamine and 0.92 g o...

Embodiment 3

[0034] Example 3: 3-bromo-N-(2-methyl-4-chloro-6-(carbamoyl)phenyl)-1-(3-chloro-2-pyridyl)-1H-pyrazole-5 - Preparation of formamide (chlorantraniliprole)

[0035] Step 1: In a 100mL three-necked flask, add 4.53g of 3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxylic acid, 1.58g of pyridine and 15mL of acetonitrile, -5°C POCl was added dropwise under the condition 3 3.07g, keep stirring for half an hour after dropping, then add 1.86g of 2-amino-3-methyl-5-chlorobenzoic acid, and react at room temperature for 0.5 hours. Add 20 mL of water and stir for 0.5 hours, filter, wash the filter cake with 3:2 acetonitrile-water, and dry to obtain 2-[3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5- Base]-6-chloro-8-methyl-4H-3,1-benzoxazin-4-one 4.07g, yield 90%.

[0036] The second step: the 2-[3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazol-5-yl]-6-chloro-8-methyl-4H obtained in the first step 4.07 g of -3,1-benzoxazin-4-one was dissolved in 20 ml of acetonitrile, then 2.73 g of triethyla...

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Abstract

The invention discloses a method for preparing N-acyl anthranilamide (I). The method comprises: reacting a substituted anthranilic acid compound (II) and a pyrazole carboxylic acid compound (III) under the action of a phosphorus reagent and a base to obtain a benzoxazinone intermediate (IV), and the latter reacts with the proton of methylamine Acid acid reaction ring-opening, obtains N-acyl anthranilamide (I), is represented as follows with reaction formula: wherein X is hydrogen, chlorine or cyano group, and HY is hydrohalic acid, sulfuric acid, phosphoric acid or carboxylic acid. The method has the advantages of simple operation, mild reaction, less three wastes, high total yield, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for preparing N-acyl anthranilamide compounds. Background technique [0002] N-acyl anthranilamide (I) is a class of important organic compounds, which are widely used in fields such as pesticides and medicines. For example, 3-bromo-N-(2-methyl-4-chloro-6-(carbamoyl)phenyl)-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-methanol Amide (X is chlorine, chlorantraniliprole) and 3-bromo-N-(2-methyl-4-cyano-6-(carbamoyl)phenyl)-1-(3-chloro-2- Pyridyl)-1H-pyrazole-5-carboxamide (X is cyano, cyantraniliprole) is two important N-acyl anthranilamide insecticides developed by DuPont, mainly acting on Insect ryanodine receptors, used to control most chewing pests, especially Lepidoptera, Coleoptera, Diptera and other pests. Applicable crops include fruit trees, vegetables, grapes, cotton, sugar cane, rice and lawns, etc. [0003] At present, the method for synthesizing N-acyl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/04
CPCC07D401/04
Inventor 关保川张天浩盛秋菊陈邦池
Owner MAX RUDONG CHEM