Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for preparing o-formamidobenzamide compound

An o-formamidobenzamide and compound technology, which is applied in the field of organic synthetic chemistry, can solve the problems of high solvent consumption, complicated post-processing, frequent replacement, etc., and achieves the effects of speeding up the reaction, inhibiting the generation of impurities and high cost

Pending Publication Date: 2022-08-09
青岛恒宁生物科技有限公司
View PDF6 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The yield of this method is acceptable, but the amount of solvent is large, the replacement is frequent, and the post-treatment is cumbersome:

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for preparing o-formamidobenzamide compound
  • Method for preparing o-formamidobenzamide compound
  • Method for preparing o-formamidobenzamide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] 1) Synthesis of methyl 2-nitro-3-methylbenzoate:

[0064] 36.9g of 2-nitro-3-methylbenzoic acid and 110.8g of dichloroethane were added to the four-necked flask, the stirring was turned on and the temperature was raised to 50°C, and 28.6g of SOCl was slowly added dropwise. 2 , after the 0.5h dropwise addition, the temperature was raised to 65°C for 0.5h, the temperature of the raw materials was lowered to 40°C after the completion of the reaction, and 7.8g methanol was added dropwise. , add 158g methanol to dissolve for later use.

[0065] 2) Synthesis of methyl 2-amino-3-methylbenzoate:

[0066] The product solution in the step (1) was transferred to the hydrogenation kettle, 0.2 g of 10% palladium carbon was added, and the hydrogenation kettle was closed. After nitrogen replacement for 3 times, 0.5 MPa hydrogen was introduced, and the stirring was started at 60 °C for reaction for 5 h. After hot filtration, the filtrate was distilled under reduced pressure to obtain...

Embodiment 2

[0076] 1) Synthesis of methyl 2-amino-5-bromo-3-methylbenzoate:

[0077] Put 30g of methyl 2-amino-3-methylbenzoate into a four-necked flask, add 100g of 50% glacial acetic acid, and add 40g of 40% hydrobromic acid dropwise with stirring at room temperature. , slowly drip 12.5g 30%H 2 O 2 , 15min was added dropwise, kept for 0.5h until the reaction was completed, 1.5g of sodium bisulfite was added, NaOH was used to adjust the pH of the system to 5-6, cooling and suction filtration, and drying to obtain 42.8g of the product. The purity determined by HPLC was 97.9%, and the yield was 94.5%.

[0078] 2) Synthesis of methyl 2-amino-5-cyano-3-methylbenzoate:

[0079] The methyl 2-amino-5-bromo-3-methylbenzoate obtained in the previous step, 200 g of N-methylpyrrolidone and 16.2 g of cuprous cyanide were put into the reaction flask, and the temperature was raised to reflux and kept for 3 to 5 hours. After completion, 120g of 15% ammonia water and 140g of dichloroethane were adde...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a method for preparing an o-formamido benzamide compound, which specifically comprises the following steps: reacting a benzoate compound with a pyridyl-substituted pyrazole acyl chloride compound in the presence of an optionally substituted pyridine compound, and carrying out ammonolysis reaction to obtain the o-formamido benzamide insecticide compound. By adopting the optionally substituted pyridine compound, the yield and the purity of the product are improved, the method has the advantages of simple route operation, relatively uniform solvent and low cost, and meanwhile, the method realizes the purposes of less generation of three wastes and stable process, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of organic synthetic chemistry, in particular to a method for preparing o-formamidobenzamide compounds. Background technique [0002] DuPont successfully developed o-formamidobenzamide insecticides in 2000, which not only have good activity against lepidopteran pests, but also have good effects on specific dipteran pests. The activity of chlorantraniliprole has broad application space and huge market prospects. The representative compound of this class of insecticides, chlorantraniliprole, is the number one insecticide in global sales. [0003] The two intermediates in the synthesis of chlorantraniliprole are mainly 2-amino-5-chloro-3-methylbenzoic acid (intermediate I) containing aromatic ring structure and 3-bromo-1-containing pyrazole ring structure (3-Chloro-2-pyridyl)-1H-pyrazole-5-carboxylic acid (Intermediate II). The existing synthetic methods mainly include the following: [0004] In the first method, anth...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04
CPCC07D401/04
Inventor 花昌林蒋振华姚明磊刘克锋葛家成王良清李建国
Owner 青岛恒宁生物科技有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com