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Method for preparing benzamide compound by using pressure reducing method

A technology for benzamides and compounds is applied in the field of preparing benzamide compounds by a reduced pressure method, and achieves the effects of inhibiting chlorinated by-products, inhibiting the generation of chlorinated by-products, and being suitable for large-scale industrial production.

Active Publication Date: 2019-07-19
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, researchers have found that when this method is used for large-scale synthesis, the bromine at the 3-position on the pyrazole undergoes a halogen cross-reaction to become chlorine, resulting in a large number of by-products of chlorobenzamides (compounds of general formula V)

Method used

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  • Method for preparing benzamide compound by using pressure reducing method
  • Method for preparing benzamide compound by using pressure reducing method
  • Method for preparing benzamide compound by using pressure reducing method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] 3-bromo-N-(2-methyl-4-chloro-6-(carbamoyl)phenyl)-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide ( Synthesis of Table 1 compound 13)

[0040]

[0041] In a 2000 ml reaction flask, add 3-bromo-1-(3-chloro-2-pyridyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid (158.6 g, 96%, 0.5 mol), 500 ml of toluene, and the reaction pressure was -0.05 MPa, and thionyl chloride (297.5 g, 2.5 mol) was added dropwise with stirring at room temperature. After the dropwise addition, stirring at room temperature was continued for 10 minutes, and then slowly heated to 50°C. After keeping at 50°C for 1 hour, the solvent was evaporated to dryness under reduced pressure to obtain 170 g of acid chloride reddish-brown oil, which was dissolved in 300 ml of acetonitrile and directly used in the next reaction.

[0042] In a 2000 ml reaction flask, 2-amino-3-methyl-5-chlorobenzamide (100.3 g, 94%, 0.475 mol), 700 ml of acetonitrile, 3-bromo-1-(3 -Chloro-2-pyridyl)-1H-pyrazole-5-formyl chloride in...

Embodiment 2

[0044] 3-Bromo-N-(2-methyl-4-cyano-6-(carbamoyl)phenyl)-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide (Table 1 Compound 23) Synthesis

[0045]

[0046]In a 2000 ml reaction flask, add 3-bromo-1-(3-chloro-2-pyridyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid (126.8 g, 96%, 0.4 mol), 400 ml of toluene, and the reaction pressure was -0.05 MPa, and thionyl chloride (238 g, 2.0 mol) was added dropwise with stirring at room temperature. After the dropwise addition, stirring at room temperature was continued for 10 minutes, and then slowly heated to 50°C. After keeping at 50°C for 1 hour, the solvent was evaporated to dryness under reduced pressure to obtain 135 g of acid chloride reddish-brown oil, which was dissolved in 240 ml of acetonitrile and directly used in the next reaction.

[0047] In a 2000 ml reaction flask, 2-amino-3-methyl-5-cyanobenzamide (76.4 g, 94%, 0.38 moles), 550 ml of acetonitrile, 3-bromo-1-( 3-Chloro-2-pyridyl)-1H-pyrazole-5-formyl chloride in acetonit...

Embodiment 3

[0049] 3-Bromo-N-(2-4,dichloro-6-(carbamoyl)phenyl)-1-(3,5-dichloro-2-pyridyl)-1H-pyrazole-5-carboxamide Synthesis of (Table 1 Compound 32)

[0050]

[0051] In a 2000 ml reaction flask, add 3-bromo-1-(3,5-dichloro-2-pyridyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid (174.74 g, 97 %, 0.5 moles), 500 milliliters of toluene, the reaction pressure is -0.055MPa, dropwise add thionyl chloride (297.5 grams, 2.5 moles) under stirring at room temperature, continue to stir at room temperature for 10 minutes after the dropwise addition, then slowly heat to 50°C . After keeping at 50°C for 1 hour, the solvent was evaporated to dryness under reduced pressure to obtain 180.2 g of acid chloride reddish-brown oil, which was dissolved in 300 ml of acetonitrile and directly used in the next reaction.

[0052] In a 2000 ml reaction flask, 2-amino-3,5-dichlorobenzamide (107.24 g, 97%, 0.475 mol), 700 ml of acetonitrile, 3-bromo-1-(3,5 -Acetonitrile solution of -dichloro-2-pyridyl)-1H-pyraz...

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Abstract

The invention relates to a method for preparing a benzamide compound represented by a general formula (I), wherein the reaction formula is defined in the specification, and each group in the formula is defined in the specification. According to the method, 3-bromo-1-(substituted pyridyl)-4,5-dihydro-1H-pyrazole-5-carboxylic acid (IV) is used as a raw material, and is simultaneously subjected to acyl chlorination and oxidation under a pressure reducing condition to prepare acyl chloride represented by a general formula (III), and the benzamide compound represented by the general formula (I) isprepared from the acyl chloride (III) and substituted aniline (II) in the absence of an acid-binding agent in a high yield manner.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for preparing benzamide compounds by a reduced pressure method. Background technique [0002] Benzamides are a class of efficient and safe new insecticides. Wherein 3-bromo-N-(2-methyl-4-chloro-6-(carbamoyl)phenyl)-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide (common name Chlorantraniliprole), 3-bromo-N-(2-methyl-4-cyano-6-(carbamoyl)phenyl)-1-(3-chloro-2-pyridyl)-1H- Pyrazole-5-carboxamide (commonly known as Cyantraniliprole.) Has high insecticidal activity, and DuPont has developed it as an insecticide. In addition, Shenyang Research Institute of Chemical Industry discovered 3-bromo-N-(2,4-dichloro-6-(carbamoyl)phenyl)-1-(3,5-dichloro-2 -pyridyl)-1H-pyrazole-5-carboxamide has also been developed as an insecticide with the common name tetraclotraniliprole. [0003] [0004] WO2009121288 A1 and CN102020633A disclose that under the action of 3-bromo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04
CPCC07D401/04
Inventor 于海波杨辉斌赵贵民陈霖李斌
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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