Synthesis method of 1-(3-chloro-2-pyridyl)-1H-pyrazole-5-formate

A synthesis method and formate technology are applied in the field of broad-spectrum insecticide chlorantraniliprole pesticides, which can solve the problems of expensive raw materials and high industrial production costs, reduce equipment corrosion and harm to the health of operators, The effect of cost reduction and mild reaction conditions

Active Publication Date: 2013-04-17
HUAIAN WAN BANG SPICE IND CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] The obvious disadvantage of this method is the use of n-butyllithium ( n -BuLi) and lithium diisopropylamide (LDA), they all need to be used under harsh reaction conditions of anhydrous, oxygen-free, and low temperature (such as - 78°C). In addition, the raw materials involved in the reaction are more expensive, and industrial production higher cost

Method used

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  • Synthesis method of 1-(3-chloro-2-pyridyl)-1H-pyrazole-5-formate
  • Synthesis method of 1-(3-chloro-2-pyridyl)-1H-pyrazole-5-formate
  • Synthesis method of 1-(3-chloro-2-pyridyl)-1H-pyrazole-5-formate

Examples

Experimental program
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Effect test

Embodiment 1

[0045] (1) Take a 50 mL three-necked flask, add a reflux condenser, and install a drying tube with anhydrous calcium chloride on the top of the condenser. Add 5 mL (123 mmol) of anhydrous methanol to the three-necked flask, add 0.54 g (10 mmol) of sodium methoxide, and when the sodium methoxide is completely dissolved, put the three-necked flask into a low-temperature reactor and cool to 0 °C. At this temperature, a mixture of methyl formate (0.78 mL, 13 mmol) and methyl pyruvate (0.75 mL, 8.3 mmol) was slowly added dropwise. After the dropwise addition was completed, the mixture was stirred at this temperature for 10 hours, and then rotary evaporated to dryness. Add 5 mL of cold diethyl ether to the evaporated solid to dissolve, filter to obtain a khaki solid sodium salt of methyl 2,4-dioxobutyrate, weigh 0.85 g after drying, and the yield is 67% (based on Calculate the amount of methyl pyruvate).

[0046](2) Take 1.52 g (10 mmol, sodium salt of methyl 2,4-dioxobutyrate) ob...

Embodiment 2

[0048] (1) Take a 50 mL three-necked flask, add a reflux condenser, and install a drying tube with anhydrous calcium chloride on the top of the condenser. Add 10 mL (246 mmol) of anhydrous methanol to the three-necked flask, and add 0.54 g (10 mmol) of sodium methoxide. When the sodium methoxide is completely dissolved, put the three-necked flask into a low-temperature reactor and cool to 0°C. At this temperature, a mixture of methyl formate (1.08 mL, 18 mmol) and methyl pyruvate (0.75 mL, 8.3 mmol) was slowly added dropwise. After the dropwise addition was complete, it was stirred at this temperature for 10 hours. Rotary evaporate to dryness, add 5 mL of cold diethyl ether to the solid, filter to obtain khaki solid sodium salt of methyl 2,4-dioxobutyrate, weigh 0.86 g after drying, and the yield is 55% (based on Calculate the amount of methyl pyruvate).

[0049] (2) Take 1.52 g (10 mmol) of methyl 2,4-dioxobutyrate sodium salt obtained in (1) above, dissolve it in 10 mL of ...

Embodiment 3

[0051] (1) Take a 50 mL three-necked flask, add a reflux condenser, and install a drying tube with anhydrous calcium chloride on the top of the condenser. Add 5 mL (123 mmol) of anhydrous methanol to the three-necked flask, and add 0.54 g (10 mmol) of sodium methoxide. When the sodium methoxide is completely dissolved, put the three-necked flask into a low-temperature reactor and cool to 0°C. At this temperature, a mixture of methyl formate (0.78 mL, 13 mmol) and methyl pyruvate (0.75 mL, 8.3 mmol) was slowly added dropwise. After the dropwise addition was complete, it was stirred at this temperature for 10 hours. Rotary evaporate to dryness, add 5 mL of cold diethyl ether to the solid, filter to obtain khaki solid sodium salt of methyl 2,4-dioxobutyrate, weigh 1.02 g after drying, and the yield is 75% (based on Calculate the amount of methyl pyruvate).

[0052] (2) Take 1.52 g (10 mmol) of methyl 2,4-dioxobutanoate sodium salt in (1) above, dissolve it in 10 mL of methanol,...

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Abstract

The invention discloses a synthesis method of 1-(3-chloro-2-pyridyl)-1H-pyrazole-5-formate. According to the synthesis method, the 1-(3-chloro-2-pyridyl)-1H-pyrazole-5-formate is prepared by condensation of 2,4-dioxobutanoate and 2-hydrazyl-3-chloropyridine, and the 2,4-dioxobutanoate is prepared by Claisen condensation of pyruvate and formate. The synthesis method disclosed by the invention has the characteristics of cheap and available raw materials, short technological process, simple operation steps, mild reaction condition, low energy consumption and low cost; besides, the synthesis method avoids poisonous raw materials adopted by a traditional method, reduces the corrosion to equipment and the danger to the health of operators; moreover, the synthesis method has little discharge of the three wastes and is beneficial to realizing the industrial application; therefore, the synthesis method disclosed by the invention is an environmentally friendly, economical and effective synthesis route.

Description

[0001] technical field [0002] The present invention relates to a broad-spectrum insecticide chlorantraniliprole pesticide, in particular to a key intermediate for synthesizing a novel ryanodine receptor insecticide chlorantraniliprole, specifically 1-(3-chloro-2-pyridyl )-1H-pyrazole-5-carboxylate synthetic method. Background technique [0003] Chlorantraniliprole (Chlorantraniliprole, commercially known as Kangkuan) is a broad-spectrum insecticide with a new structure (bisamide / pyrazole). The biggest feature of this insecticide is that it only acts on the ryanodine receptor (RyR) in insects. Because of the structural difference between this receptor and the ryanodine receptor in mammals, it has no effect on mammals. The toxicity is very low; and because chlorantraniliprole has the ability to quickly prevent pests from eating, high-efficiency retention activity and excellent resistance to rain erosion, it can achieve quick-acting and good long-term plant protection. At p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04
Inventor 安礼涛姜育田周建峰杨志坚支三军陈雄安小伟黄其赞
Owner HUAIAN WAN BANG SPICE IND CO LTD
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