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Halogenated nicotinic acid ester compound and synthesis method thereof

A technology of halogenated nicotinic acid esters and synthesis methods, which is applied in the field of halogenated nicotinic acid ester compounds and their synthesis, and can solve the problems of a large amount of waste salt, a large amount of waste water, and high energy consumption

Active Publication Date: 2022-07-01
QINGDAO RAINBOW CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the route of amination first, alkaline acid-binding agents are usually used, which is prone to produce a large amount of waste salt, etc.; the route of etherification first will also produce a large amount of waste water and waste salt
[0010] To sum up: the existing technology has many reaction steps, complicated operation, high energy consumption, and produces a large amount of three wastes at the same time. If proper process optimization is carried out, it has important industrial production value

Method used

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  • Halogenated nicotinic acid ester compound and synthesis method thereof
  • Halogenated nicotinic acid ester compound and synthesis method thereof
  • Halogenated nicotinic acid ester compound and synthesis method thereof

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[0038] The embodiment of the present invention provides a method for synthesizing halogenated nicotinic acid ester compounds as described above, comprising the following steps:

[0039] The halogenated nicotinic acid or its derivative is reacted with the meta-substituted phenol to obtain the halogenated nicotinic acid ester compound having the general structural formula of formula I;

[0040] The halogenated nicotinic acid is preferably 2-chloronicotinic acid or 2-iodonicotinic acid, more preferably 2-chloronicotinic acid; the substituent in the meta-substituted phenol is -CF 3 , -CCl 3 , -CI 3 , -CH 3 , -OCH 3 or -OOCCH 3 , preferably -CF 3 .

[0041] Specifically, in the embodiment of the present invention, X is Cl and R is -CF 3 Taking the substance 3-(trifluoromethyl)phenyl 2-chloronicotinate as an example, two methods for synthesizing 3-(trifluoromethyl)phenyl 2-chloronicotinate are provided. In some embodiments of the present invention, the synthetic method speci...

Embodiment 1

[0090] Add 15.7g (0.1mol) 2-chloronicotinic acid (purity: 99.5%), 150mL tetrahydrofuran (purity: 99.5%), 18g (0.11mol) CDI (purity: 99%) into the reaction flask, heat to reflux and stir for 2h Then, 18.01 g (0.11 mol) of 3-trifluoromethylphenol (purity: 99%) was added dropwise, and the reaction was refluxed for 6 h, and the reaction was completed. Washed with 50 mL of 10% liquid caustic soda (sodium hydroxide, purity: 96%), washed twice with 50 mL of water, evaporated the solvent to dryness to obtain 28.13 g of colorless oil, yield: 91%, purity 97.2% (high performance liquid chromatography) ).

[0091] The NMR image of 3-(trifluoromethyl)phenyl 2-chloronicotinate is shown in figure 1 ;

[0092] NMR characterization: 1 H-NMR (CDCl 3 , 500MHz): 8.67 (dd, 1H), 8.43 (dd, 1H), 7.59-7.50 (m, 2H), 7.53 (s, 1H), 7.44-7.41 (m, 1H).

Embodiment 2

[0094] Add 15.7g (0.1mol) 2-chloronicotinic acid (purity: 99.5%), 150mL tetrahydrofuran (purity: 99.5%), 18g (0.11mol) CDI (purity: 99%) into the reaction flask, heat to reflux and stir for 2h , and then dropwise added 21.28 g (0.13 mol) of 3-trifluoromethylphenol (purity: 99%), refluxed for 8 h, and the reaction was completed. 50mL of 10% liquid caustic soda (sodium hydroxide, purity: 96%) was washed, 50mL of water was washed twice, and the solvent was evaporated to dryness to obtain 28.25g of colorless oil, yield: 91%, purity 97.1% (high performance liquid chromatography). ).

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Abstract

The invention provides a halogenated nicotinic acid ester compound which has a structural general formula I, in the formula I, X is preferably-Cl or-I; in the formula, R is-CF3,-CCl3,-CI3,-CH3,-OCH3 or-OOCCH3. The invention provides a synthesis method of the compound. The halogenated nicotinate substance as shown in the formula I belongs to a novel compound, and the structure of 3-(trifluoromethyl) phenyl 2-chloronicotinate is as shown in the formula I-1, namely, in the formula I, X is chlorine, and R is-CF3; the compound can be used as an important intermediate for synthesizing a pesticide diflufenican, and can be used for synthesizing the diflufenican with 2, 4-difluoroaniline under certain conditions, and the specific reaction equation is as follows. When the halogenated nicotinic acid ester compound provided by the invention is used for synthesizing diflufenican, the production is efficient, and environmental protection is facilitated.

Description

technical field [0001] The invention belongs to the technical field of pesticide synthesis, in particular to a halogenated nicotinic acid ester compound and a synthesis method thereof. Background technique [0002] Diflufenican (diflufenican), also known as diflufenican, the English name is diflufenican, the chemical name is N-(2,4-difluorophenyl)-2-[(3-trifluoromethyl)phenoxy Base]-3-pyridinecarboxamide, CAS No. 83164-33-4, belongs to substituted pyridyl anilide herbicides, mainly used in corn, soybean and wheat fields to control a variety of annual grass weeds and some broadleaf weeds Grass. The function of diflufenamide is to inhibit the biosynthesis of carotenoids by inhibiting phytoene dehydrogenase; and it can be compounded with a variety of herbicides to expand the herbicidal spectrum and improve the herbicidal effect. The chemical structural formula of diflufenac is as follows: [0003] [0004] At present, there are two main process routes for the synthesis of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/80C07D213/803C07D213/82
CPCC07D213/80C07D213/803C07D213/82Y02P20/55
Inventor 袁良国李现顺程朝阳
Owner QINGDAO RAINBOW CHEM CO LTD