Synthesis method of 2-cyano-N-(2, 4-dichloro-5-methoxyphenyl) acetamide

A technology of methoxyphenyl and synthesis method, which is applied in the field of compound chlorination synthesis, can solve the problems of cumbersome post-treatment, poor selectivity, and difficult process, and achieve the effects of cost control, mild reaction conditions, and good selectivity

Inactive Publication Date: 2013-03-06
大连九港生物科技有限公司
View PDF8 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The method reported in the literature above uses the raw material 2,4-dichloro-5-methoxyaniline, which is often obtained by chlorination of m-methoxyaniline, which has poor selectivity and high cost; the solvent used is tetrahydrofuran, which is expensive and difficult to recycle; During the reaction process, 1,3-diisopropylcarbodiimide is quantitatively added as a dehydrating agent. After the reaction is completed, it is difficult to completely remove it after treatment, which makes the post-treatment more cumbersome. The cost of the entire process is high and it is difficult to process.

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
  • Synthesis method of 2-cyano-N-(2, 4-dichloro-5-methoxyphenyl) acetamide
  • Synthesis method of 2-cyano-N-(2, 4-dichloro-5-methoxyphenyl) acetamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Preparation of II:

[0013] Add m-methoxyaniline 123g and ethyl cyanoacetate 180g to a 1000mL four-necked flask equipped with mechanical stirring, a thermometer and a condenser, and start stirring; the temperature is raised to 200°C, and the temperature is kept for 4h; the reaction solution is lowered to room temperature, and there are The solid was precipitated and filtered; the filter cake was washed with solvent to obtain II181.7g, the yield was 95.6%.

[0014] Preparation of III:

[0015] Add Ⅱ190.2g and 1250mL chloroform to a 1000mL jacketed kettle equipped with mechanical stirring, thermometer, air pipe and exhaust gas absorption, turn on stirring, and cool down to -5℃; 255.6g was introduced in about 4h; the reaction was complete, the system was purged with nitrogen, and the material was filtered; the filter cake was washed with water to obtain 242.6g of the target product III crude product; the solvent was recrystallized and dried to obtain 230.5g of solid produ...

Embodiment 2

[0017] Preparation of II:

[0018] Add m-methoxyaniline 123g and ethyl cyanoacetate 339g to a 1000mL four-necked flask equipped with mechanical stirring, a thermometer and a condenser, and start stirring; the temperature is raised to 180°C, and the temperature is kept for 4h; the reaction solution is lowered to room temperature, and there are The solid was precipitated and filtered; the filter cake was washed with solvent to obtain II 182.4 g with a yield of 96%.

[0019] Preparation of III:

[0020] In a 1000mL jacketed kettle equipped with mechanical stirring, thermometer, gas pipe and exhaust gas absorption, add Ⅱ190.2g, 1,2-dichloroethane 1250mL, turn on stirring, cool down to 0℃; pass chlorine gas, and control the temperature at 0 ~5°C, 284g was introduced in about 4h; the reaction was complete, the system was purged with nitrogen, and the material was filtered; the filter cake was washed with water to obtain 231.7g of the target product III crude product; the solvent wa...

Embodiment 3

[0022] Preparation of II:

[0023] Add m-methoxyaniline 123g and ethyl cyanoacetate 226g to a 1000mL four-necked flask equipped with mechanical stirring, a thermometer and a condenser, and start stirring; heat up to 150°C, and keep the temperature for 6h; lower the reaction solution to room temperature, and there are The solid was precipitated and filtered; the filter cake was washed with solvent to obtain II 171 g with a yield of 90%.

[0024] Preparation of III:

[0025] Add Ⅱ190.2g and 1250mL ethyl acetate into a 1000mL jacketed kettle equipped with mechanical stirring, thermometer, gas pipe and exhaust gas absorption, and start stirring; pass chlorine gas, control the temperature at 10-20℃, and pass 284g in about 4h; The reaction was completed, the system was purged with nitrogen, and the material was filtered; the filter cake was washed with water to obtain 232 g of the target product III crude product; the solvent was recrystallized and dried to obtain 215 g of solid pr...

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 belongs to the field of organic chloride compounds in organic chemistry, and relates to a chlorination synthesis technology of a compound, in particular to a synthesis method of 2-cyano-N-(2, 4-dichloro-5-methoxyphenyl) acetamide. The synthesis method comprises the following operation steps of: adding m-methoxyaniline and ethyl cyanoacetate into a four-mouth flask, starting to stir and controlling temperature to be 120-200 DEG C and time to be 2-8 hours, wherein the molar ratio of the m-methoxyaniline to the ethyl cyanoacetate is 1:1-5; cooling reaction solution to room temperature, separating out solid and filtering to obtain a rough product II; washing the rough product II though a solvent to obtain II; adding a solvent and II into a jacketed kettle and starting to stir, wherein the mass ratio of the II to the solvent is 1:2-6; introducing chlorine gas and controlling temperature to be 20 DEG C below zero to 20 DEG C and time to be 2-6 hours, wherein the molar ratio of the chlorine gas to the II is 1:2-6; and fully reacting, blowing a system through nitrogen gas, discharging, filtering, washing filter cake to obtain a target product, a rough product III. The synthesis method has the advantages of cheap and readily available raw materials, mild reaction conditions, high yield and good selectivity and is a synthesis method with extremely high industrial value.

Description

technical field [0001] The invention belongs to the field of organic chlorine compounds in organic chemistry, and relates to the technology of compound chlorination synthesis. Background technique [0002] The synthetic literature of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide adopts the reaction of cyanoacetic acid and 2,4-dichloro-5-methoxyaniline, 1, 3-Diisopropylcarbodiimide was used as dehydrating agent, tetrahydrofuran was used as solvent, and the yield was 88% (J.Med.Chem.2006, 49, 7868-7876, US2005043537A1) [0003] The method reported in the literature above uses the raw material 2,4-dichloro-5-methoxyaniline, which is often obtained by chlorination of m-methoxyaniline, which has poor selectivity and high cost; the solvent used is tetrahydrofuran, which is expensive and difficult to recycle; During the reaction process, 1,3-diisopropylcarbodiimide is quantitatively added as a dehydrating agent. After the reaction is completed, it is difficult to completely re...

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): C07C255/19C07C253/30
Inventor 王海英秦学孔于滨刘传科
Owner 大连九港生物科技有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap