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Synthesis method of N-cyanomethyl-4-(trifluoromethyl)-nicotinamide

A technology of trifluoromethyl nicotinic acid and trifluoromethyl, which is applied in the field of pesticides, can solve problems such as hydrolysis of acid chlorides, and achieve the effects of good yield, improved safety, and simple operation

Pending Publication Date: 2019-06-07
JINGBO AGROCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The invention provides a synthetic method of N-cyanomethyl-4-(trifluoromethyl)nicotinamide, which solves the problem of reacting the acyl chloride with aminoacetonitrile hydrochloride with 4-trifluoromethyl nicotinic acid, and the acyl chloride will There is a problem of hydrolysis, which improves the purity and yield of the product, reduces the production cost, improves the production safety, and facilitates the realization of industrial production

Method used

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  • Synthesis method of N-cyanomethyl-4-(trifluoromethyl)-nicotinamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Add 15g (0.075mol) of 4-trifluoromethylnicotinic acid and 7.5g of toluene into a 250mL reactor with a reflux condenser, cool down to 5°C in ice water, and slowly add 2.88g (0.025mol) of methanesulfonyl chloride dropwise , No new products were detected by liquid phase detection, and the reaction temperature was raised to 20°C, and triethylamine was slowly added dropwise to the reaction system, and the reaction was stopped for 6 hours until no raw materials were tracked. Add 50 g of water to wash after the reaction, and dissolve the acid anhydride in the toluene layer for subsequent use.

[0030] In another 250ml reactor, add aminoacetonitrile hydrochloride 2.6g (0.0275mol), toluene 20g, cool to 0-5 ℃ in ice water, dropwise add 30% concentration of liquid caustic soda solution 7.45g, add 2.6 g sodium bicarbonate solid, then slowly drop the mixed acid anhydride obtained in the previous step into the system, react for 4 hours, and after liquid phase detection and tracking o...

Embodiment 2

[0032] Add 11g (0.055mol) of 4-trifluoromethylnicotinic acid and 2.2g of dichloroethane into a 250mL reactor with a reflux condenser, cool the ice water to 5°C, and slowly add 5.75g (0.050mol) Methanesulfonyl chloride, no new product was formed by liquid phase detection, and the reaction temperature was raised to 20°C, and triethylamine was slowly added dropwise to the reaction system, and the reaction was stopped for 8 hours until no raw materials were tracked. Add 50 g of water to wash after the reaction, and dissolve the acid anhydride in the dichloroethane layer for subsequent use.

[0033] In another 250ml reactor, add 4.3g (0.046mol) of aminoacetonitrile hydrochloride, 20g of dichloroethane, cool to 0-5°C in ice water, dropwise add 7.45g of 30% concentration of liquid caustic soda solution, and dropwise end Finally, add 3.45g of potassium carbonate solid, and then slowly drop the mixed acid anhydride obtained in the previous step into the system, react for 3 hours, liqui...

Embodiment 3

[0035] Add 5g (0.025mol) of 4-trifluoromethylnicotinic acid and 0.625g of N-methylpyrrolidone into a 250mL reactor with a reflux condenser, cool the ice water to 5°C, and slowly add 0.572g (0.005mol) ) methanesulfonyl chloride, no new product was generated by liquid phase detection, and the temperature of the system was raised to 40°C, and 3-picoline was slowly added dropwise to the reaction system, and the reaction was stopped for 6.5 hours until no raw materials were tracked. Add 50 g of water to wash after the reaction, and dissolve the acid anhydride in the toluene layer for subsequent use.

[0036] In another 250ml reactor, add aminoacetonitrile hydrochloride 1.576g (0.0166mol), N-methylpyrrolidone 20g, cool to 0-5 ℃ in ice water, dropwise add 7.45g of liquid caustic soda solution of 30% concentration, dropwise After the completion, add 0.66g of pyridine, then slowly drop the mixed acid anhydride obtained in the previous step into the system, react for 5.5h, liquid phase ...

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Abstract

The invention discloses a synthesis method of N-cyanomethyl-4-(trifluoromethyl)-nicotinamide, and belongs to the technical field of pesticides. According to the method, 4-trifluoromethylnicotinic acidand methane sulfonyl chloride are taken as the primary raw materials and carry out reactions in the presence of an acid binding agent and a solvent to prepare acid anhydrides; then in the presence ofan acid binding agent, acid anhydrides and amino acetonitrile hydrochloride carry out reactions to prepare N-cyanomethyl-4-(trifluoromethyl)-nicotinamide. 4-trifluoromethylnicotinic acid and methanesulfonyl chloride are taken as the primary raw materials to synthesize acid anhydrides at first, acid anhydrides are resistant to hydrolysis, then acid anhydrides react with amino acetonitrile hydrochloride to prepare N-cyanomethyl-4-(trifluoromethyl)-nicotinamide; the conversion rate is high (not less than 96%); the purity is high, and the yield is good (not less than 90%). Toxic phosgene is notused, the safety is greatly improved, moreover, the operation is simple, and the synthesis method is suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of pesticides, in particular to a synthesis method of N-cyanomethyl-4-(trifluoromethyl)nicotinamide. Background technique [0002] N-cyanomethyl-4-(trifluoromethyl)nicotinamide, English common name: flonicamid, Chinese common name: flonicamid. N-cyanomethyl-4-(trifluoromethyl)nicotinamide is a novel low-toxic pyridine amide insect growth regulator insecticide, and its preparation is 10% water-dispersible granule. N-cyanomethyl-4-(trifluoromethyl)nicotinamide is effective against various piercing-sucking mouthparts pests and has good penetration. It can penetrate from roots to stems and leaves, but the penetration from leaves to stems and roots is relatively weak. The agent works by hindering the sucking action of pests. The pests stop sucking soon after ingesting the potion, and finally die of starvation. According to the preparation method of N-cyanomethyl-4-(trifluoromethyl) nicotinamide reported in do...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/82
Inventor 成道泉韦能春王祥传
Owner JINGBO AGROCHEM TECH CO LTD
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