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Method for preparing flonicamid

A technology of flonicamid and amidation reaction, which is applied in the field of medicinal chemistry, can solve problems such as unsuitable for industrialized production, difficult to realize industrialized, unfavorable for industrialized production, etc., and achieve significant application value, low risk, and simplified operation

Inactive Publication Date: 2020-11-13
厦门优孚利生物医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Above route is the method that industrial production adopts at home and abroad at present, although direct method has few steps, yield is low (43.5%), and product is difficult to purify, and laboratory needs to purify with column chromatography, and industrialization is difficult to realize; The purity is higher, but the steps are long, the yield (55.7%) is low, and it is not suitable for industrialized production; although the above method is mature and the raw materials are easy to get, the amount of "three wastes" is relatively large and the yield is low, which is not conducive to industrialized production

Method used

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  • Method for preparing flonicamid
  • Method for preparing flonicamid
  • Method for preparing flonicamid

Examples

Experimental program
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Effect test

Embodiment 1

[0051] The specific steps for preparing flonicamid in this example are: add (95.5g, 0.5mol) compound of formula I and (94.5g, 0.5mol) compound of formula III in a 500ml four-necked reaction flask, and add as organic solvent A Dichloromethane 150ml, cool down to 0-10°C in an ice-water bath, and slowly add triethylamine (50.55g, 0.5mol) as an acid-binding agent dropwise at a controlled temperature of 0-10°C, and add (105g, 0.5mol) after the addition is complete Formula II compound, heat up to 30-35 ° C for 4 hours, add 50 g of water dropwise after the reaction is complete, separate layers, adjust the organic layer to PH = 7-8 with liquid caustic, then separate layers, distill the organic layer under reduced pressure, and distill After completion, add 250ml of absolute ethanol as organic solvent B, slowly cool down to 0-5°C, filter and dry with suction to obtain 206.1g of the target compound IV as a dry product, with a molar yield of more than 90% and a purity of more than 98%.

Embodiment 2

[0053]The specific steps for preparing flonicamid in this example are: add (95.5g, 0.5mol) compound of formula I and (54.26g, 0.5mol) compound of formula III in a 500ml four-necked reaction flask, and add as organic solvent A Dichloroethane 150ml, cool down to 0-10°C in an ice-water bath, slowly add triethylamine (50.55g, 0.5mol) dropwise as an acid-binding agent at a controlled temperature of 0-10°C, and drop (105g, 0.5mol) ) Formula II compound, warming up to 30-35°C for 4 hours, adding 50g of water dropwise after the reaction is complete, layering, adjusting the organic layer to PH=7-8 with liquid caustic, then layering, and distilling the organic layer under reduced pressure, After the distillation, add 250ml of absolute ethanol as organic solvent B, slowly cool down to 0-5°C, filter and dry to obtain 207.1g of the target compound IV as a dry product, with a molar yield of over 90.4% and a purity of over 98%.

Embodiment 3

[0055] The specific steps for preparing flonicamid in this example are: add (95.5g, 0.5mol) compound of formula I and (54.26g, 0.5mol) compound of formula III in a 500ml four-necked reaction flask, and add as organic solvent A Toluene 150ml, cool down to 0-10°C in an ice-water bath, and slowly add triethylamine (50.55g, 0.5mol) as an acid-binding agent dropwise at a controlled temperature of 0-10°C, and then add (105g, 0.5mol) of formula II Compound, heat up to 30-35°C and keep warm for 4 hours. After the reaction is complete, 50g of water is added dropwise, and the layers are separated. The organic layer is adjusted to PH=7-8 with liquid caustic soda, and then the layers are separated. The organic layer is distilled under reduced pressure, and the toluene is evaporated. After 100ML, slowly lower the temperature to 0-5°C, filter and dry with suction to obtain 205g of the target compound IV as a dry product, with a molar yield of over 89.5% and a purity of over 98%.

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Abstract

The invention discloses a method for preparing flonicamid. The method comprises the following steps: S1, condensation reaction: in an organic solvent A, carrying out condensation reaction on a compound in a formula I and a compound in a formula III under the action of an acid-binding agent; wherein the organic solvent A is halogenated hydrocarbon or aromatic hydrocarbon; and S2, amidation reaction: after the condensation reaction in the step S1 is completed, directly adding a compound shown in a formula II without separation to carry out amidation reaction so as to obtain a compound shown in aformula IV. The intermediate one-pot method is adopted for continuous reaction to prepare flonicamid, the intermediate does not need to be purified, a target compound can be obtained only through simple operation, the feeding ratio is reduced, raw materials are saved, cost is saved, and operation is simplified. The method has the advantages of mild operation and adjustment, low risk, cheap and easily available raw materials, reduction of the generation and treatment of three wastes, realization of the high-purity flonicamid from the final product, realization of the total yield reaching 90% or above, great significance in the large-scale preparation of flonicamid, and meeting of the requirements of industrial large-scale production.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a method for preparing flonicamid. Background technique [0002] Fluonicamid (flonicamid) is a pyridinamide (or nicotinamide) insecticide discovered by Japan Ishihara Sangyo Co., Ltd. It can effectively control piercing-sucking mouthparts pests on a wide range of crops, especially for aphids. Its mechanism of action is novel, it has no cross-resistance with other insecticides currently on the market, and has low toxicity to bees. Its market prospect is worth looking forward to. The structural formula of flonicamid is as follows: [0003] [0004] At present, there are mainly two methods for the synthesis of flonicamid: direct method and indirect method. [0005] Direct method: Synthesize acid chloride from 4-trifluoromethylnicotinic acid and thionyl chloride as raw materials, and then react with aminoacetonitrile sulfate to obtain flonicamid. The chemical reactio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/82
CPCC07D213/82
Inventor 黄振辉林峰陶平
Owner 厦门优孚利生物医药科技有限公司
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