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A technology of chlorantraniliprole and chlorpyridine, which is applied in the field of preparation of chlorantraniliprole, can solve the problems of tedious synthesis steps and low yield of chlorantraniliprole
Active Publication Date: 2021-03-26
CHONGQING HUAGE BIOCHEM
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[0006] The present invention intends to provide a preparation method of chlorantranil...
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Embodiment 1
[0034] A preparation method of chlorantraniliprole, the synthesis reaction of chlorantraniliprole is shown in formula (i), specifically comprising the following steps.
[0035]
[0036] Step 1, the synthesis of 3,6-dichloro-2-hydrazinopyridine:
[0037] Add 2,3,6-trichloropyridine (60g, 0.33mol) and 80% hydrazine hydrate solution (96.6g, 1.55mol) successively into a 500mL four-neck flask equipped with a reflux tube, and add the mixture under stirring at room temperature Catalyst A, catalyst A can be copper chloride, cuprous chloride, tetrabutyl ammonium chloride, benzyl trimethyl ammonium chloride, tetramethyl ammonium chloride, triphenyl butyl phosphorus bromide, triethyl ammonium chloride One or more of methyl ammonium chloride, tetramethyl ammonium bromide, benzyl triethyl ammonium chloride, tetrabutyl ammonium iodide. Catalyst A in this example is tetrabutylammonium chloride (1.8g, 0.006mol). After adding catalyst A, the temperature is raised to 108-110°C, and the refl...
Embodiment 2
[0065] A preparation method of chlorantraniliprole, the synthesis reaction of chlorantraniliprole is shown in formula (i), specifically comprising the following steps.
[0066] Step 1, the synthesis of 3,6-dichloro-2-hydrazinopyridine.
[0067] The difference between this step and step one in Example 1 is: in this step, the addition amount of 80% hydrazine hydrate solution is 90.1g (1.44mol), and catalyst A is cuprous chloride (0.6g, 0.006mol) , reflux reaction for 4 hours, the filter cake was washed with clear water to neutrality and then washed twice with ethanol, and the product 3,6-dichloro-2-hydrazinopyridine was obtained after drying 55.3g, and the HPLC normalized content was 98% (analysis conditions : The chromatographic column is a C18 silica gel reverse-phase column 4.6x150mm 5 μm, the mobile phase is acetonitrile:water:acetic acid=1:1:1%), and the yield is 92.3%.
[0068] Step 2, the synthesis of 3-chloro-2-hydrazinopyridine.
[0069] The difference between this st...
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Abstract
The invention relates to the field of insecticide synthesis, and discloses a preparation method of chlorantraniliprole. The preparation method comprises the following steps: synthesis of an intermediate I, synthesis of an intermediate II and synthesis of chlorantraniliprole. The method comprises the following steps: reacting 2, 3, 6-trichloropyridine serving as a raw material with hydrazine hydrate under the action of a catalyst A to obtain 3, 6-dichloro-2-hydrazinopyridine, carrying out hydrogenation reduction reaction under the action of a catalyst B to obtain an intermediate I, reacting theintermediate I with diethyl maleate, and preparing the 2-(3-chloropyridine-2-yl)-5-hydroxypyrazole-3-ethyl formate under the action of a catalyst C, and hydrolyzing after bromination to obtain an intermediate II, and preparing chlorantraniliprole from the intermediate II. According to the invention, 2, 3, 6-trichloropyridine is adopted to replace 2, 3-dichloropyridine as a raw material to preparethe intermediate I, so that the defects of difficulty in obtaining the 2, 3-dichloropyridine raw material, harsh synthesis conditions, low yield and the like are avoided, the total reaction yield ofthe intermediate I is improved, the intermediate II is prepared by a one-pot method, the post-treatment operation is reduced, and the synthesis cost of chlorantraniliprole is reduced.
Description
technical field [0001] The invention relates to the field of insecticide synthesis, in particular to a preparation method of chlorantraniliprole. Background technique [0002] Chlorantraniliprole, trade name: Kangkuan, ISO common name is Chlorantraniliprole, developed by DuPont Company of the United States in 2000, as a new type of high-efficiency, low-toxicity insecticide, widely used in the control of Lepidoptera pests . It belongs to the ryanodine receptor agent, which selectively activates the ryanodine receptor in the muscle of the pest, excessively releases intracellular calcium ions, and causes the paralysis and death of the pest. The insecticide has broad spectrum, high efficiency, safety and low toxicity. [0003] At present, there are many preparation methods of chlorantraniliprole, for example, patent WO2006062978A1 discloses 3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxylic acid and substituted o-aminobenzene Formamide, in the presence of methanesulfonyl...
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