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Synthesis method of chlorantraniliprole intermediate

A technology for the synthesis of chlorantraniliprole and its synthesis method, which is applied in the field of synthesis of chlorantraniliprole intermediates, can solve the problems of difficult treatment of three wastes, many reaction steps, and low purity, and achieve large-scale industrial production, The effect of mild reaction conditions and simplified reaction steps

Active Publication Date: 2021-10-22
内蒙古灵圣作物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Aiming at the problems that the synthesis method of chlorantraniliprole intermediate in the prior art has many reaction steps, low yield and purity, and the difficulty in processing the three wastes generated, the present invention provides a chlorantraniliprole intermediate resolve resolution

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  • Synthesis method of chlorantraniliprole intermediate
  • Synthesis method of chlorantraniliprole intermediate
  • Synthesis method of chlorantraniliprole intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] A kind of synthetic method of chlorantraniliprole intermediate:

[0040] Add 86.88g of phosphorus oxybromide (0.3mol, content 99%) and 137.60g of valeronitrile into a dry four-necked flask, stir for 10min, add 27.52g of 2-(3-chloro-pyridin-2-yl)-5-oxo Ethyl-pyrazolidine-3-carboxylate (0.10mol, content 98%), slowly warming up to 125-130°C, keeping the temperature for 5h, then removing 98wt% of valeronitrile under reduced pressure, cooling to 5-10°C, Add 137.6g of water and stir, filter with suction, and dry the filter cake to obtain 31.59g of ethyl 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylate, off-white powder , yield 94.99%, liquid chromatography purity 99.40%. After the reaction, the liquid phase detection spectrum of the reaction feed liquid is as follows: figure 1 shown.

[0041] 1 HNMR(DMSO,43MHz)δ:8.59-7.74(2H,m),7.74-6.87(2H,m),3.89(2H,q,J=7.1Hz),3.04(1H,s),2.25(1H,q , J=1.9Hz), 0.81 (3H,t, J=7.1Hz). Melting point: 117.0-117.5°C.

Embodiment 2

[0043] A kind of synthetic method of chlorantraniliprole intermediate:

[0044] Add 289.3g of phosphorus oxybromide (1mol, content 99%) and 413.00g of dichlorobutane into a dry four-necked flask, stir for 10min, add 137.60g of 2-(3-chloro-pyridin-2-yl)-5- Oxo-pyrazolidine-3-ethyl carboxylate (0.50mol, content 98%), slowly warming up to 125-130°C, keeping the temperature for 5h, then removing 98wt% of dichlorobutane under reduced pressure, cooling to 5- 10°C, add 412.80g of water, stir, filter with suction, and dry the filter cake to obtain 157.44g of ethyl 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylate, Off-white powder, yield 94.30%, liquid chromatography purity 99.00%.

[0045]1 HNMR(DMSO,43MHz)δ:8.59-7.74(2H,m),7.74-6.87(2H,m),3.89(2H,q,J=7.1Hz),3.04(1H,s),2.25(1H,q , J=1.9Hz), 0.81 (3H,t, J=7.1Hz). Melting point: 117.2-117.6°C.

Embodiment 3

[0047] A kind of synthetic method of chlorantraniliprole intermediate:

[0048] Add 144.80g of phosphorus oxybromide (0.50mol, content 99%) and 139.00g of phenylacetonitrile into a dry four-necked flask, stir for 10min, add 27.80g of 2-(3-chloropyridin-2-yl)-5-oxo -Pyrazolidine-3-ethyl carboxylate (0.10mol, content 98%), slowly warming up to 100-105°C, keeping the temperature for 8h, then removing 90wt% of phenylacetonitrile under reduced pressure, cooling to 10-15°C, adding 139.29g of water was suction-filtered, and the filter cake was dried to obtain 31.28g of ethyl 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylate as off-white powder. The yield is 93.65%, and the liquid chromatography purity is 98.97%.

[0049] 1 HNMR(DMSO,43MHz)δ:8.59-7.74(2H,m),7.74-6.87(2H,m),3.89(2H,q,J=7.1Hz),3.04(1H,s),2.25(1H,q , J=1.9Hz), 0.81 (3H,t, J=7.1Hz). Melting point: 117.0-117.4°C.

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Abstract

The invention relates to the technical field of chemical synthesis, and particularly discloses a synthesis method of a chlorantraniliprole intermediate. The synthesis method comprises the following steps: under the condition of an organic solvent, taking a compound I and phosphorus oxybromide as raw materials, and carrying out bromination and oxidation one-step reaction to prepare a compound II. Under the condition of a specific solvent, the compound I and phosphorus oxybromide in a specific proportion are used as raw materials, the compound II is prepared through one-step reaction, the product with the purity larger than 98.5% can be obtained only through simple aftertreatment of the reaction product, the yield can reach 92% or above, the raw materials are few in variety, the production cost is low, the amount of three wastes generated in the reaction process is small, and the method is green and environment-friendly and suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a method for synthesizing an intermediate of chlorantraniliprole. Background technique [0002] Chlorantraniliprole is a high-efficiency, broad-spectrum, low-toxic o-formamidobenzamide insecticide developed by DuPont in 2000. The chemical name is 3-bromo-N-[4-chloro-2 -Methyl-6-(methylcarbamoyl)phenyl]-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide, the structural formula is shown in formula III. [0003] [0004] 3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid ethyl ester is an important intermediate of chlorantraniliprole, and its structural formula is shown in formula II. 3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid ethyl ester is first hydrolyzed to generate 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyridine azole-5-carboxylic acid, and then react with 2-amino-5-chloro-N,3-dimethylformamide to generate chlorantraniliprole. At pr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04
CPCC07D401/04
Inventor 康茹梦刘少华冯亚惠张优张超李娟
Owner 内蒙古灵圣作物科技有限公司