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Method for preparing chiral hexaconazole

A hexaconazole and chiral technology, applied in the field of preparing chiral hexaconazole, can solve the problems of being unsuitable for large-scale industrial production, complicated routes, harsh conditions, etc., and achieve a low dosage, high product purity, and easy operation. Effect

Active Publication Date: 2010-08-18
合肥华纳生物医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the currently reported methods for the synthesis of chiral hexaconazole have complex routes, harsh conditions, and high costs, which are not suitable for large-scale industrial production.

Method used

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  • Method for preparing chiral hexaconazole
  • Method for preparing chiral hexaconazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] 1) Synthesis of 1-(2,4-dichlorophenyl)-1-pentene (B)

[0051] Dissolve 100mmol of 1-(2,4-dichlorophenyl)-1-pentanone (23.1g) in pre-dried toluene, keep the temperature at -20°C, and add 150mmol of methylenetriphenyl to the system dropwise Phosphorus ylide (41.5g) in toluene solution (concentration is 1mol / L); after dropwise addition, slowly warm up to room temperature, and stir at room temperature for 6h; raw material 1-(2,4-dichlorophenyl)- When the content of 1-pentanone is less than 1%, the reaction ends. After the reaction is completed, 0.6 mol of water is added to the reaction system to quench the reaction, and distillation under reduced pressure gives 21.7 g of 1-(2,4-dichlorophenyl)-1-pentane Alkene (B), yield 95%;

[0052] (2) Synthesis of epoxidized intermediate (C)

[0053] 100mmol 1-(2,4-dichlorophenyl)-1-pentene (22.9g) and catalytic amount of titanium tetraisopropoxide (5×10 -4 mol) was dissolved in DMF, and the temperature was kept at 10°C, and 150mmol ...

Embodiment 2

[0057] 1) Synthesis of 1-(2,4-dichlorophenyl)-1-pentene (B)

[0058] Dissolve 100mmol of 1-(2,4-dichlorophenyl)-1-pentanone (23.1g) in pre-dried dioxane, keep the temperature at -10°C, and add 200mmol of methylene dropwise to the system Triphenylphosphorus ylide (55.3g) in dioxane solution (concentration is 1mol / L); after the dropwise addition, slowly warm up to room temperature, and stir at room temperature for 8h; raw material 1-(2,4- When the content of dichlorophenyl)-1-pentanone is less than 1%, the reaction ends. After the reaction is completed, 1mol of water is added to the reaction system to quench the reaction, and distillation under reduced pressure obtains 21.3g 1-(2,4-dichlorophenyl )-1-pentene (B), yield 93.1%;

[0059] (2) Synthesis of epoxidized intermediate (C)

[0060] 100mmol 1-(2,4-dichlorophenyl)-1-pentene (22.9g) and catalytic amount of salen-Mn complex (1×10 -4 mol) was dissolved in toluene, and the temperature was kept at 0°C, and 150mmol mCPBA (25.9g...

Embodiment 3

[0064] 1) Synthesis of 1-(2,4-dichlorophenyl)-1-pentene (B)

[0065] Dissolve 100mmol 1-(2,4-dichlorophenyl)-1-pentanone (23.1g) in pre-dried THF, keep the temperature at 0°C, and add 300mmol methylenetriphenylphosphine dropwise to the system Yelide (82.8g) in THF solution (concentration: 1mol / L); after the dropwise addition, slowly warm up to room temperature, and stir at room temperature for 4 hours; the raw material 1-(2,4-dichlorophenyl)-1 was analyzed by gas chromatography - When the pentanone content is less than 1%, the reaction ends, after the reaction is completed, 1.2mol of water is added to the reaction system to quench the reaction, and distillation under reduced pressure obtains 22.3g 1-(2,4-dichlorophenyl)-1-pentene (B), yield 97.2%;

[0066] (2) Synthesis of epoxidized intermediate (C)

[0067] 100mmol 1-(2,4-dichlorophenyl)-1-pentene (22.9g), catalytic amount of titanium trichloride (5×10 -4 mol) and 2,3-naphthyridine ligand (5×10 -4 mol) was dissolved in d...

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Abstract

The invention provides a method for preparing chiral hexaconazole, comprising the following steps of: leading 1-(2, 4-dichlorophenyl)-1-pentanone and methylene triphenylphosphine to have ylide reaction, and generating 1-(2, 4-dichlorophenyl)-1-pentene; leading the 1-(2, 4-dichlorophenyl)-1-pentene and epoxidation reagent to have reaction under the action of transition metal catalyst, and generating epoxidation intermediate; and finally, carrying out ring opening between the epoxidation intermediate and 1, 2, 4-triazole, and obtaining (-)-hexaconazole. The chiral hexaconazole prepared by the method has high optical purity and the e. e% more than 80%; and furthermore, the total reaction yield is more than 75%, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for preparing the pesticide hexaconazole, in particular to a new method for preparing chiral hexaconazole. Background technique [0002] Optically active pesticides are currently one of the more active research directions in the field of pesticide chemistry in the world. According to the latest statistics, 28% of the commercialized agrochemicals are chiral compounds; among the more than 170 kinds of chiral pesticides that have been commercialized, there are more than 30 kinds with annual sales of more than 100 million US dollars, and those with annual sales of more than 25 million US dollars. There are more than 60 kinds, among which the sales of chiral pesticides containing highly active chiral isomers exceed 10 billion US dollars, and the annual sales of chiral pesticides with pure optically active isomers are close to 3 billion US dollars. 35% of the pesticide market share. [0003] From the perspective of biologi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/08
Inventor 刘迎春高源
Owner 合肥华纳生物医药科技有限公司
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