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Composite method of triketone compound

A synthesis method and compound technology, applied in the synthesis of mesotrione and sulcotrione, can solve the problems of long reaction time and incomplete rearrangement reaction, and achieve the effects of high product yield, environmental friendliness and low toxicity

Active Publication Date: 2010-06-16
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main disadvantage of this route is that the rearrangement reaction is not complete and the reaction time is long

Method used

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  • Composite method of triketone compound
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  • Composite method of triketone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Preparation of sulcotrione: In a three-necked flask, add 328g (1.0mol) 3-(2-chloro-4-thiamphenicol benzoyloxy)-2-cyclohexene-1-one, 2L 1,2 -Dichloroethane, 222.6g (2.2mol) triethylamine, 6.8g (0.05mol) 6-hydroxypurine, stirred, heated, the reaction temperature was 45-50°C, reacted for 5h, cooled, acidified with 10% hydrochloric acid, Make the pH value <1, statically separate the layers, and desolventize the organic phase to obtain 278 g of sulcotrione, with a yield of 85%.

Embodiment 2

[0021] Preparation of mesotrione: In a three-necked flask, add 339g (1.0mol) 3-(2-nitro-4-thiamphenicol benzoyloxy)-2-cyclohexen-1-one, 2.5L 1 , 2-dichloroethane, 222.6g (2.2mol) triethylamine, 6.8g (0.05mol) 6-hydroxypurine, stirring, heating, reaction temperature at 45-50°C, reaction for 5h, cooling, and 10% hydrochloric acid Acidify to make the pH value < 1, static layering, and desolvation of the organic phase to obtain 284.6 g of mesotrione, with a yield of 84%.

Embodiment 3-5

[0023] With reference to the method of Example 1, the consumption of triethylamine was changed, and other reaction conditions were the same as in Example 1 to obtain sulcotrione, and the results are shown in Table 1.

[0024] Table 1: Influence of the amount of triethylamine on the reaction

[0025] Example

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Abstract

The invention discloses a composite method of triketone compound shown in the formula (I). In the formula (I), X is Cl or NO2. The composite method is as follows: enol ester shown in the formula (II) generates rearrangement reaction under the action of an alkaline reagent and a rearrangement catalyst in organic solvent; after reaction ends, the obtained reaction liquid is acidized and separated to obtain the triketone compound; the rearrangement catalyst is purine compound. The composite method of the triketone compound (sulcotrione and mesotrione) of the invention adopts the catalyst with small toxicity, protects environment, has high product yield and is suitable for industrial production.

Description

(1) Technical field: [0001] The invention relates to a synthesis method of triketone compounds, especially a synthesis method of sulcotrione and mesotrione. (two) background technology: [0002] Triketone herbicides (sulcotrione, mesotrione) are mainly used to control broad-leaved weeds and gramineous weeds in corn and other crop fields. It has very low toxicity and no phytotoxicity to subsequent rotation crops. [0003] The existing synthetic methods mainly use the corresponding enol esters as starting materials to prepare sulcotrione and mesotrione through the rearrangement of rearrangement reagents under alkaline conditions. For example, US patents (US4762551, US4775411 and US20030232984) reported that using triethylamine as an alkaline reagent, the corresponding enol esters were rearranged to generate sulcotrione and mesotrione under the action of acetone cyanohydrin. The main disadvantage of this route is that the rearrangement reagent acetone cyanohydrin is highly to...

Claims

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Application Information

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IPC IPC(8): C07C317/24C07C315/04
Inventor 杜晓华骆大为徐振元
Owner ZHEJIANG UNIV OF TECH
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