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Chlorantraniliprole preparation method

A technology for chlorantraniliprole and chlorobenzoic acid, applied in the field of preparation of chlorantraniliprole, can solve problems such as long reaction route and low cost, and achieve the effects of reducing dosage, mild conditions and improving product yield

Inactive Publication Date: 2013-04-24
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0017] The reaction route of this method is shown in the figure above, using monomethyl maleate as the starting material, no special reagents are required, the cost is low, the reaction conditions are relatively mild, and the post-treatment is relatively simple, but this reaction route is relatively long

Method used

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Synthesis of N-2-methylbenzene-2-isonitrosoacetamide (2)

[0037]

[0038] Solution A: A 250 ml three-neck round bottom flask, equipped with a condensing device and a thermometer, added hydroxylamine hydrochloride (3.5 g, 50 mmol), anhydrous sodium sulfate (23.7 g, 167 mmol), chloral hydrate (2.7 g, 16.3 mmol), 67 ml of water. Heat to 40°C with vigorous stirring to dissolve. Solution B: o-toluidine (1.8 g, 16.8 mmol) was added dropwise to a solution containing 15 ml of water and 1.5 ml of concentrated hydrochloric acid. Add solution B to solution A at one time, stir rapidly and heat to reflux. After 1-2 min, the mixture turns milky white, accompanied by a small amount of white precipitates of brown by-products. Remove the oil bath, and cool the ice bath to room temperature (20 ° C), after standing overnight at room temperature, the precipitate was obtained by suction filtration, washed with ice water, and dried with phosphorus pentoxide to obtain 2.24 g of a yellow...

Embodiment 2

[0040] Synthesis of 7-methylindole-2,3-dione (3) Synthesis

[0041]

[0042] In the 50 ml three-neck round-bottomed flask equipped with a condenser tube and a thermometer, add 26.5 ml of concentrated sulfuric acid, heat to 60 ° C, and add N-2-methylbenzene-2-isonitrosoacetamide ( 6.7 g, 37.6 mmol), keep the temperature between 60-70 ° C, the solution turns purple, after the addition, it is warming up to 80 ° C and stirred for 10 min, the reaction is stopped, cooled at room temperature, and the reaction solution is poured under stirring On 160 g of crushed ice, let it stand overnight, and filter with suction to obtain a rust-colored precipitate, dissolve the rust-colored precipitate in 12 ml of hot water, add NaOH solution (that is, dissolve 1.4 g of sodium hydroxide in 5 ml of H 2 O) to make it dissolve, then adjust the pH to 3 with 4 M hydrochloric acid solution, and precipitate occurs, filter, and the filter residue is a black substance, continue to adjust the pH of the f...

Embodiment 3

[0044] Synthesis of 5-chloro-7-methylindole-2,3-dione

[0045]

[0046] (1) Add 1.2 g (7.5 mmol) 7-methylindole-2,3-dione and 18 ml glacial acetic acid into a 50 ml three-neck flask, stir for 5 minutes, the solution turns wine red, but there are still some solids insoluble. Add 1.5 ml (18.5 mmol) of sulfuryl chloride dropwise to the reaction solution at room temperature, heat in an oil bath, and the solid dissolves at an internal temperature of 65 °C, continue heating to an internal temperature of 118 °C, reflux for 3 hours, stop the reaction, cool to room temperature and pour into crushed ice, extracted with dichloromethane, dried, and rotary evaporated to obtain 1.24 g of a brick-red solid, with a yield of 85.1%. 1 H NMR (400 MHz, DMSO-d 6 ) : δ = 2.17 (s, 3H, CH 3 ), 7.37 (s, 1H, Ar-H), 7.51 (s, 1H, Ar-H), 11.20 (s, 1H, NH).

[0047] (2) Add 1.2 g (7.5 mmol) 7-methylindole-2,3-dione and 18 ml glacial acetic acid into a 50 ml three-neck flask, stir for 5 minutes, th...

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Abstract

The invention discloses a chlorantraniliprole preparation method. A technical scheme adopted by the invention is characterized in that the chlorantraniliprole preparation method comprises the follow synthetic steps: 1, 2-amino-3-methyl-5-chlorobenzoate synthesis; 2, 3-bromo-1-(3-chloropyridine-2-pyridyl)-1H-pyrazole-5-formic acid synthesis; and 3, chlorantraniliprole synthesis. The invention concretely relates to synthetic methods of the key chlorantraniliprole intermediates comprising 2-amino-3-methyl-5-chlorobenzoate and 3-bromo-1-(3-chloropyridine-2-pyridyl)-1H-pyrazole-5-formic acid. The synthetic method of the pesticide chlorantraniliprole has the advantages of low cost, high yield, strong operability, realization of the industrialized production, and the like.

Description

technical field [0001] The invention relates to a synthesis process of an insecticide, in particular to a preparation method of chlorantraniliprole. Background technique [0002] Chlorantraniliprole, Chinese trade name: Kangkuan, is a new type of high-efficiency, low-toxic o-formamidobenzamide insecticide developed by DuPont in 2000. Good insecticidal activity, with special effects on Lepidoptera insects. The chemical name (CAS) is: 3-bromo-N-{4-chloro-2-methyl-6-[(methylamino)carbonyl]phenyl}-1-(3-chloro-2-pyridyl)-1H -Pyridine-5-amide, English common name: chlorantraniliprole, test code DPX-E2Y45, CAS registration number: 500008-45-7, molecular formula: C 18 h 14 BrCl 2 N 5 o 2 , relative molecular mass: 483.1, and its chemical structure is as follows: [0003] [0004] 1. As the key intermediate for the synthesis of Kangkuan, 2-amino-3-methyl-5-chlorobenzoic acid has been reported successively by domestic and foreign literature in the synthesis of Kangkuan and i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04
Inventor 李伟郑文涛姜玉钦张玮玮王晓锦赵丽萍徐桂清
Owner HENAN NORMAL UNIV
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