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Synthetic process of hydramethylnon

A synthetic process, the technology of hydrazone, which is applied in the field of new synthetic technology of hydrazone, can solve the problems of unavailable, expensive catalysts, etc., and achieve the effects of mild reaction conditions, low cost and safe production process

Active Publication Date: 2016-04-13
JIANGXI ANLIDA CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The catalyst used in this synthetic route is expensive and difficult to obtain, which limits industrialization to a certain extent

Method used

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  • Synthetic process of hydramethylnon
  • Synthetic process of hydramethylnon
  • Synthetic process of hydramethylnon

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] A kind of synthetic technique of embodiment 1 hydrazone

[0039] Step I. Synthesis of 5,5-dimethyl-1,4,5,6-tetrahydropyrimidin-2-one

[0040]

[0041] Add 70.5g (0.5mol) of 2,2-dimethyl-1.3-dichloropropane, 150ml of toluene, and 45g (0.75mol) of urea into a 500ml four-necked reaction flask, heat it, and add triethylamine dropwise under reflux Amine 75.6g (0.75mol), after the dropwise addition, continue to reflux for 4h; after the reaction, at 50°C, distill off the toluene under reduced pressure, add an appropriate amount of water to the residue, and extract twice with dichloromethane, 50ml each time , combined dichloromethane pages, washed with water, dried over magnesium sulfate, and concentrated to dryness to obtain 121.5 g of the title compound (white solid), yield 84%;

[0042] m / z:129[M+1] + .

[0043] Step II. Synthesis of 2-hydrazino-5,5-dimethyl-1,4,5,6-tetrahydropyrimidine hydrochloride

[0044]

[0045]Add 64.0g (0.5mol) of 5,5-dimethyl-1,4,5,6-tetra...

Embodiment 2

[0056] Step I. Synthesis of 5,5-dimethyl-1,4,5,6-tetrahydropyrimidin-2-one

[0057]

[0058] Add 70.5g (0.5mol) of 2,2-dimethyl-1.3-dichloropropane, 150ml of chloroform, and 36g (0.60mol) of urea into a 500ml four-necked reaction flask, heat it, and add triethylamine dropwise under reflux Amine 75.6g (0.75mol), after the dropwise addition, continue to reflux for 6h; after the reaction, add an appropriate amount of water, extract the water layer with chloroform twice, 50ml each time, combine the chloroform phases, wash with water, dry over magnesium sulfate, and concentrate to dryness The title compound 110g (white solid) was obtained with a yield of 76%;

[0059] m / z:129[M+1] + .

[0060] Step II. Synthesis of 2-hydrazino-5,5-dimethyl-1,4,5,6-tetrahydropyrimidine hydrochloride

[0061]

[0062] Add 64.0g (0.5mol) of 5,5-dimethyl-1,4,5,6-tetrahydropyrimidine- 2-ketone, 24g (0.6mo1) 80% hydrazine hydrate. Stir at room temperature until it becomes transparent, then heat...

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Abstract

The invention provides a synthetic process of hydramethylnon. The synthetic process comprises the steps of preparing 2-hydrazino-5,5-dimethyl-1,4,5,6-tetrahydro pyrimidin hydrochloride and 1,5-bis(4-trifluoromethylphenyl)-1,4-pentadiene-3-ketone, and taking the two as raw materials and taking isopropyl alcohol or ethyl alcohol as a solvent to generate the hydramethylnon under the action of concentrated hydrochloric acid. According to the synthetic process provided by the invention, through changing the synthetic process, reaction efficiency is improved, the yield of the 2-hydrazino-5,5-dimethyl-1,4,5,6-tetrahydro pyrimidin hydrochloride is increased to not less than 90 percent from 78 percent, and the yield of the 1,5-bis(4-trifluoromethylphenyl)-1,4-pentadiene-3-one is also increased to not less than 90 percent from 83 percent reported in literature.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry and pesticide technical preparation, and in particular relates to a new synthesis process of hydrazone. Background technique [0002] Hydramethylnon, chemical name: Tetrahydro-5,5-dimethyl-2(1H)-pyrimidinone-[3-[4-(trifluoromethyl)phenyl]-1-[2- [4-(trifluoromethyl)phenyl]vinyl]-2-propenylene]hydrazone; English name: 1,4-Pentadien-3-one,1,5-bis[4-(trifluoromethyl)phenyl ]-,2-(1,4,5,6-tetrahydro-5,5-dimethyl-2-pyrimidinyl)hydrazone, the structural formula is shown in 1. [0003] [0004] Hydrazone is a new type of hygienic insecticide discovered and produced by American Cyanamid Corporation. It mainly relies on the energy generated by specifically destroying insect cells to kill insects. It has the characteristics of high efficiency and low toxicity and the elimination of "chain poisoning". Cockroach effect, becoming the World Health Organization (WHO) recommended pesticides that can ...

Claims

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Application Information

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IPC IPC(8): C07D239/18
CPCC07D239/18
Inventor 范恩荣高荣明高勤伟
Owner JIANGXI ANLIDA CHEM CO LTD
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