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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
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  • 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

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  • 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...

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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

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Application Information

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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
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