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Novel 2-aryloxynicotinamide compound, and preparation method and application of same

A technology for aryloxynicotinamide and amide compounds, which is applied in the application field of synthesizing diflufenicin and 2-aryloxynicotinic acid compounds, and can solve the problem of expensive, harsh and chlorine-containing waste water waste from starting materials and other problems, to achieve the effect of easy control of the operation process, good herbicidal activity, and simple and easy-to-obtain reaction raw materials

Inactive Publication Date: 2020-03-10
NANJING AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The conditions used in this route are relatively harsh, the starting materials are expensive, and more chlorine-containing wastewater or waste will be produced.

Method used

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  • Novel 2-aryloxynicotinamide compound, and preparation method and application of same
  • Novel 2-aryloxynicotinamide compound, and preparation method and application of same
  • Novel 2-aryloxynicotinamide compound, and preparation method and application of same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1: Synthesis of Nicotinamide Compound C1

[0038]

[0039] Weigh the o-(4,5-dihydro-2-oxazolyl)aniline intermediate B1 (1mmol), niacin (1mmol), and 4-dimethylaminopyridine DMAP (0.2mmol) in a 50mL eggplant-shaped flask, Dissolve in 5 mL of dichloromethane (DCM), add condensing agent EDCI (1.2 mmol) under ice bath, stir at room temperature, thin layer chromatography (TLC) to track and monitor the reaction process, about 6h after treatment. Add 10 mL of water to quench the reaction, separate the layers and extract with dichloromethane (15 mL×3). After the dichloromethane phases are combined, they are washed with water (10 mL×2) and saturated sodium chloride solution (10 mL×2). Anhydrous sulfuric acid The sodium was dried, the solvent was evaporated under reduced pressure, and after silica gel column chromatography (eluent: petroleum ether / ethyl acetate = 10:1), compound C1 was obtained with a yield of 74%. LC-MS(ESI+)m / z: Calcd.for[M+H: C 15 H 14 N 3 O 2 ]: 268.11, ...

Embodiment 2

[0040] Example 2: Synthesis of 2-aryloxynicotinamide compound D1

[0041] Weigh nicotinamide compound C1 (1mmol), sodium carbonate (2mmol) and copper nitrate (0.5mmol) into the reaction flask, add DMSO (5mL), and then add 3-trifluoromethylphenol ( 3mmol), react at 80°C for 8 hours, cool to room temperature, add ethyl acetate (EtOAc, 20mL) to dilute, then add (28%-30%) ammonium hydroxide (NH 3 ·H 2 O, 8mL) solution into the reaction system, continue to stir for 20min, and extract with ethyl acetate (EtOAc, 20mL×3), the organic phases were combined and washed with saturated sodium bicarbonate solution (NaHCO 3 , 10mL×3), washed with water (10mL×3), saturated sodium chloride (NaCl, 10mL×3) solution, washed the organic phase with anhydrous sodium sulfate (Na 2 SO 4 ) After drying and concentration, column chromatography (V Petroleum ether : V Ethyl acetate =12:1) to obtain a white solid D1 with a yield of 71%.

[0042]

[0043] LC-MS(ESI+)m / z: Calcd.for[M+H: C 22 H 17 F 3 N 3 O 3 ]: 4...

Embodiment 3

[0045] Example 3: Synthesis of 2-aryloxynicotinic acid compound E1

[0046]

[0047] Weigh 2-(3-trifluoromethyl)phenoxynicotinamide compound D1 (1mmol) and sodium hydroxide (40mmol) into the reaction flask, add 5mL ethanol, and react at 80℃ for 6h. After the reaction is complete, Evaporate the organic solvent, add water, extract with ethyl acetate (EtOAc) (15mL×3), combine the organic phases and add anhydrous sodium sulfate to dry, concentrate and column chromatography (eluent: V Petroleum ether : V Ethyl acetate =20:1), 125 mg of oxazolinamine B1 was recovered, and the yield was 77.6%. Add 1M hydrochloric acid (HCl) solution to the aqueous phase, adjust the pH to 4, extract with ethyl acetate (EtOAc) (15mL×3), add anhydrous sodium sulfate to dry, concentrate and column chromatography (eluent: V Petroleum ether : V Ethyl acetate = 2:1) to obtain 2-(3-trifluoromethyl)phenoxynicotinic acid E1 with a yield of 84%.

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Abstract

The invention relates to a novel 2-aryloxynicotinamide compound, and a preparation method and an application of same, wherein the 2-aryloxynicotinamide compound has a chemical structural formula as the formula (I). With nicotinic acid being initial raw material, the compound is prepared through a condensation reaction and a carbon-hydrogen bond direct etherification. The invention can provide a new method for preparing the 2-aryloxynicotinamide compounds and derivatives thereof, which can be used for preparing an herbicide, diflufenican. The compounds show excellent herbicidal activity and have a potential as an herbicide applied to agricultural-related fields. In the general formula (I), the carbon atom connected to the substitution group R has a spatial configuration of R or S, Ar representing an aryl substitution group (detailed in the specification).

Description

Technical field [0001] The present invention belongs to the technical field of chemical and pesticide technology; in particular, it refers to the preparation method of 2-aryloxynicotinamide compounds, the application of herbicides in the field of plant protection, and the use of intermediates in the synthesis of diflufenican and 2-aryl compounds. Application of oxynicotinic acid compounds. Background technique [0002] 2-Aryloxynicotinamide compounds occupy an important position in medicinal chemistry and pesticide chemistry. Such compounds have significant biological activities such as antibacterial, weeding, insecticide, and anti-cancer. At the same time, this skeleton can also be used as a multifunctional Framework or organic intermediates are used in the design, synthesis and structure-activity relationship research of new nicotinamide compounds. Diflufenican (diflufenican) is a typical representative of 2-aryloxynicotinamide compounds developed into pesticides. Its CAS regi...

Claims

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Application Information

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IPC IPC(8): C07D413/12C07D213/82C07D213/80C07D213/803A01N43/76A01N43/40A01P13/00
CPCC07D413/12C07D213/82C07D213/80C07D213/803A01N43/76A01N43/40
Inventor 李圣坤宋泽华王国通李伟
Owner NANJING AGRICULTURAL UNIVERSITY
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