Catalyst for catalyzing synthesis of indoxacarb key intermediate and application of catalyst

A technology for catalyzing indanes and catalysts, which is applied in the directions of organic compound/hydride/coordination complex catalysts, physical/chemical process catalysts, organic chemistry, etc., and can solve the problems of large amount of catalyst, high production cost, low catalyst efficiency, etc. , to achieve the effect of enhancing selectivity, reducing dosage, and facilitating industrialization

Active Publication Date: 2019-11-29
JINGBO AGROCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] First, cinchona base catalysts such as cinchonin are used, but the efficiency of this type of catalyst is low, and the S body content of the synthesized indoxacarb original drug is about 70%;
[0005] Second, metal complex catalysts are used. In 2007, DuPont Company of the United States reported a metal zirconium catalyst, but this type of catalyst is used in a large amount, and the production cost is high, and the S body content of the obtained indoxacarb original drug is about 90%. ;

Method used

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  • Catalyst for catalyzing synthesis of indoxacarb key intermediate and application of catalyst
  • Catalyst for catalyzing synthesis of indoxacarb key intermediate and application of catalyst
  • Catalyst for catalyzing synthesis of indoxacarb key intermediate and application of catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Prepare a chiral catalyst and use the catalyst to prepare indoxacarb. The specific preparation method is as follows:

[0040] (1) Add 3.26g (0.01mol) of quinidine hydrochloride to a 1000mL clean and anhydrous reaction flask, then add 50mL of toluene, heat up to 60°C and stir to dissolve.

[0041] (2) Weigh 1.25 g (0.01 mol) of manganese chloride, and add it to the toluene solution of the above-mentioned hydroquinidine.

[0042] (3) Heating up to 80° C., reacting for 2 hours to obtain a clear and transparent chiral catalyst solution.

[0043] The method for preparing S-body indoxacarb using the above-mentioned catalyst can adopt the conventional synthesis route disclosed in the master’s degree thesis "Synthetic Technology and Polymorphic Form of Novel and High-efficiency Chiral Insecticide Indoxacarb" awarded by Zhejiang University in 2014. in:

[0044] (4) Add 225g tert-butyl hydroperoxide and 449g 5-chloro-2-methoxycarbonyl-1-indanone ester and 500mL toluene to the c...

Embodiment 2

[0047] Prepare a chiral catalyst and use the catalyst to prepare indoxacarb. The specific preparation method is as follows:

[0048] (1) Add 4.89g (0.015mol) of quinidine hydrochloride to a 1000mL clean and anhydrous reaction flask, then add 50mL of toluene, heat up to 60°C and stir to dissolve.

[0049] (2) Weigh 1.51 g (0.01 mol) of manganese sulfate, and add it into the above-mentioned toluene solution of quinidine hydrochloride.

[0050] (3) Heating up to 80° C., reacting for 2 hours to obtain a clear and transparent chiral catalyst solution.

[0051] The method for preparing S-body indoxacarb using the above-mentioned catalyst can adopt the conventional synthesis route disclosed in the master’s degree thesis "Synthetic Technology and Polymorphic Form of Novel and High-efficiency Chiral Insecticide Indoxacarb" awarded by Zhejiang University in 2014. in:

[0052] (4) add 113g tert-butyl hydroperoxide and 224g 5-chloro-2-methoxycarbonyl-1-indanone ester and 600mL toluene t...

Embodiment 3

[0055] Prepare a chiral catalyst and use the catalyst to prepare indoxacarb. The specific preparation method is as follows:

[0056] (1) Add 6.52g (0.02mol) of quinidine hydrochloride to a 1000mL clean and anhydrous reaction flask, then add 50mL of toluene, heat up to 60°C and stir to dissolve.

[0057] (2) Weigh 0.89g (0.01mol) of manganese hydroxide, and add it into the above-mentioned toluene solution of quinidine hydrochloride.

[0058] (3) Heating up to 80° C., reacting for 2 hours to obtain a clear and transparent chiral catalyst solution.

[0059] The method for preparing S-body indoxacarb using the above-mentioned catalyst can adopt the conventional synthesis route disclosed in the master’s degree thesis "Synthetic Technology and Polymorphic Form of Novel and High-efficiency Chiral Insecticide Indoxacarb" awarded by Zhejiang University in 2014. in:

[0060] (4) add 169g tert-butyl hydroperoxide and 336g 5-chloro-2-methoxycarbonyl-1-indanone ester and 600mL toluene to...

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PUM

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Abstract

The invention relates to the field of chemical synthesis, and particularly discloses a catalyst for catalyzing the synthesis of an indoxacarb key intermediate and application of the catalyst. According to the catalyst, metal in metal compounds such as a manganese compound, a copper compound and a zirconium compound is used as a coordination center, cinchona alkaloid chiral compounds such as dihydroquinidine (DHQD) are used as ligands to form a chiral complex catalyst, the novel catalyst is applied to an asymmetric synthesis reaction of tert-butyl hydroperoxide and 5-chloro-2-methoxycarbonyl-1-indanone ester, the selectivity in the asymmetric synthesis process is greatly improved, and the content of an S-form is increased from 75% to 99% or above; and moreover, the use amount of the catalyst is low, a synthesis process is simple, it is conducive to industrialization, and a good foundation is laid for production of high-quality indoxacarb.

Description

technical field [0001] The invention relates to the field of chemical synthesis, and specifically discloses a catalyst for catalyzing the synthesis of key intermediates of indoxacarb and its application. Background technique [0002] Indoxacarb is a new type of oxadiazine insecticide with high efficiency and low toxicity developed by DuPont Company of the United States. It has dual effects of contact killing and stomach poisoning, and can effectively solve resistant pests. It has no cross-resistance with other insecticides such as pyrethroids, organophosphorus, and carbamates, and can well solve the problems of rice leaf rollers, rice stem borers and resistant diamondback moths that are difficult to control in the market. In addition, indoxacarb has a very wide insecticidal spectrum, and one drug can prevent multiple diseases. While preventing and controlling noctuid pests, it also has a good inhibitory effect on mirid bugs, so it is a very good comprehensive management tool...

Claims

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Application Information

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IPC IPC(8): C07D453/04B01J31/22C07D273/04
CPCC07D453/04B01J31/2208C07D273/04B01J2531/72B01J2531/0261C07B2200/07
Inventor 薄蕾芳张芳芳冯培良刘建成于连友成道泉王祥传
Owner JINGBO AGROCHEM TECH CO LTD
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