Synthesis method of flonicamid

A technology of flonicamid and the flonicamid, which is applied in the field of synthesizing flonicamid, can solve the problems of long steps, low product purity, complicated process, etc. simple effect

Pending Publication Date: 2021-08-17
HUBEI JINGHONG CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The yield of this method is low, and product purification is difficult; the indirect method is also to first synthesize acid chloride, then react with methyleneamino acetonitrile, and then obtain flonicamid after multi-step reaction
However, the above two methods have low yields, large pollution, long steps and complex processes, and the product has low purity and difficult purification.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] In the reaction flask, add 50g (0.261mol) of 4-trifluoromethylnicotinic acid, 250mL of dichloromethane, 76.7g (0.958mol) of sodium bicarbonate and 5.9g of benzyltriethylammonium chloride (0.025mol) and mix Solution, add 38.8g (0.338mol) of methanesulfonyl chloride dropwise at low temperature 0°C, then add 31.4g (0.339mol) of aminoacetonitrile hydrochloride, then add 50g of water dropwise, raise the temperature to reflux at 38-40°C, and the central control will display After the reaction was complete (about 1.5 hours), 200 mL of water was added dropwise, and the temperature was lowered to 5° C. and stirred for 1 hour. Filtration and drying yielded 56.5 g of the product flonicamid, with a purity of 99.2%, a water content of 0.33%, and a yield of 95.2%.

[0020] Precautions

[0021] Although the reaction is a water addition reaction, it is still necessary to control the moisture in the reaction system before adding aminoacetonitrile hydrochloride, otherwise the methanesul...

Embodiment 2

[0027] In a 500mL three-necked reaction flask, add 20g (0.104mol) of 4-trifluoromethylnicotinic acid, 100mL of dichloromethane, 30.8g (0.385mol) of sodium bicarbonate and 2.3g of benzyltriethylammonium chloride (0.01mol ) mix, stir evenly, add 15.5g (0.135mol) of methanesulfonyl chloride dropwise at a low temperature of 0°C, then add 12.6g (0.135mol) of aminoacetonitrile hydrochloride, then add 20g of water dropwise, heat up to 38-40°C and reflux After the central control showed that the reaction was complete (about 1.5 hours), 80 mL of water was added dropwise, and then the temperature was lowered to 5°C and stirred for 1 hour. Filtration and drying yielded 22.5 g of the product flonicamid, with a purity of 99.5%, a water content of 0.18%, and a yield of 93.7%.

Embodiment 3

[0029] In a 500mL three-necked reaction flask, add 20g (0.104mol) of 4-trifluoromethylnicotinic acid, 100mL of dichloromethane, 30.8g (0.385mol) of sodium bicarbonate and 1.2g of benzyltriethylammonium chloride (0.005mol ) mix, stir evenly, add 15.5g (0.135mol) of methanesulfonyl chloride dropwise at a low temperature of 0°C, then add 10.7g (0.114mol) of aminoacetonitrile hydrochloride, then add 20g of water dropwise, heat up to 38-40°C and reflux After the central control showed that the reaction was complete (about 1.5 hours), 80 mL of water was added dropwise, and then the temperature was lowered to 5°C and stirred for 1 hour. Filtration and drying yielded 22.0 g of the product flonicamid, with a purity of 99.6%, a water content of 0.22%, and a yield of 92.1%.

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Abstract

The invention discloses a synthesis method of flonicamid, and belongs to the technical field of organic synthesis. 4-trifluoromethyl nicotinic acid and aminoacetonitrile hydrochloride are subjected to a reflux reaction in a dichloromethane and water mixed system in the presence of a mixed catalytic system, after water is added for crystallization, filtration and drying are performed to obtain a white crystal flonicamid product, the purity can reach 99.0% or above, and the white crystal flonicamid product is dried, sealed and stored. The method is simple in route operation, few in reaction by-products, high in product purity, low in cost and high in market competitiveness.

Description

technical field [0001] The invention relates to a method for synthesizing flonicamid, which belongs to the technical field of organic synthesis. Background technique [0002] Flunicamid, white crystal, melting point: 157-158°C, CAS 158062-67-0, molecular formula C 9 h 6 f 3 N 3 O, is a new type of low toxicity pyridine amide insect growth regulator insecticide. [0003] The methods in the prior art are divided into direct method and indirect method. The direct method is to first make 4-trifluoromethyl nicotinic acid into acid chloride, and then react with aminoacetonitrile hydrochloride. The yield of this method is low, and product purification is difficult; the indirect method is also to first synthesize acid chloride, then react with methyleneamino acetonitrile, and then obtain flonicamid after multi-step reaction. However, the yields of the above two methods are all low, the pollution is large, the steps are long and the process is complicated, and the product has lo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/82
CPCC07D213/82
Inventor 黄谊田智勇杨辉朱美山杨超
Owner HUBEI JINGHONG CHEM
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