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Preparation method of trifloxystrobin characteristic impurity

A technology of trifloxystrobin and impurities, which is applied in the field of organic compound preparation, can solve the problems of low yield of target products, and achieve the effects of good quality control, no side reactions, and high yield

Pending Publication Date: 2021-10-22
长沙嘉桥生物科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Pasumpon Kamaraj et al. used a one-pot method to synthesize the above-mentioned trifloxystrobin characteristic impurity, but a large amount of alkali was used in this synthesis method, and the addition of alkali and bromoxime ether at the same time would decompose part of the bromoxime ether, thus resulting in the loss of the target product. Low yield (Pasumpon Kamaraj et al., Letters in Organic Chemistry, 2015, 12, 306-310)

Method used

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  • Preparation method of trifloxystrobin characteristic impurity
  • Preparation method of trifloxystrobin characteristic impurity
  • Preparation method of trifloxystrobin characteristic impurity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] This example provides a characteristic impurity of trifloxystrobin (E)-2-((E)-2-methoxy-1-(methoxyimino)-2-ethoxy)phenyl-2-(methoxy The preparation method of oxyimino)-2-(2-(((E)-1-(3-(trifluoromethyl)phenyl)ethyleneamino)methoxy)phenyl)acetic acid methyl ester, specifically Proceed as follows:

[0053] (1) Synthesis of Sodium Oxygenate

[0054]

[0055] Add 620.1g DMF and 206.9g trifloxystrobin (external standard content is 98%) in reaction kettle, start to stir, then heat up to 30 ℃, slowly add 21.8g sodium hydroxide (96%, 0.525mol), after reacting for 5h After the reaction was detected by HPLC (normalized raw material98%), the reaction solution I was obtained.

[0056] (2) Synthesis of characteristic impurities of trifloxystrobin

[0057]

[0058] Add a total of 174.8g bromoxime ether (90%, 0.55mol) in batches to the reaction solution I obtained in step (1), carry out the condensation reaction at 30°C, take a sample for detection, until the sodium oxalate is...

Embodiment 2

[0064] This example provides a characteristic impurity of trifloxystrobin (E)-2-((E)-2-methoxy-1-(methoxyimino)-2-ethoxy)phenyl-2-(methoxy The preparation method of oxyimino)-2-(2-(((E)-1-(3-(trifluoromethyl)phenyl)ethyleneamino)methoxy)phenyl)acetic acid methyl ester, specifically Proceed as follows:

[0065] (1) Synthesis of Sodium Oxygenate

[0066]

[0067] Add 784.3g DMF and 207.1g trifloxystrobin (external standard content is 98%) in reaction kettle, start to stir, then heat up to 60 ℃, slowly add 20.8g sodium hydroxide (96%, 0.5mol), after reacting for 2h After the reaction was detected by HPLC (normalized raw material98%), the reaction solution I was obtained.

[0068] (2) Synthesis of characteristic impurities of trifloxystrobin

[0069]

[0070] Add a total of 190.9g bromoxime ether (90%, 0.6mol) in batches to the reaction solution I obtained in step (1), carry out the condensation reaction at 60°C, take a sample for detection, until the sodium oxalate is co...

Embodiment 3

[0076] This example provides a characteristic impurity of trifloxystrobin (E)-2-((E)-2-methoxy-1-(methoxyimino)-2-ethoxy)phenyl-2-(methoxy The preparation method of oxyimino)-2-(2-(((E)-1-(3-(trifluoromethyl)phenyl)ethyleneamino)methoxy)phenyl)acetic acid methyl ester, specifically Proceed as follows:

[0077] (1) Synthesis of Sodium Oxygenate

[0078]

[0079] Add 1000.4g DMF and 206.5g trifloxystrobin (external standard content is 98%) in reaction kettle, start to stir, then heat up to 90 ℃, slowly add 25.1g sodium hydroxide (96%, 0.6mol), after reaction 1h After completion of the HPLC detection reaction (normalized raw material98%), the reaction solution I was obtained.

[0080] (2) Synthesis of characteristic impurities of trifloxystrobin

[0081]

[0082] Add a total of 238.8g bromoxime ether (90%, 0.75mol) in batches to the reaction solution I obtained in step (1), carry out condensation reaction at 90°C, take samples for detection, until the sodium oxalate is com...

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Abstract

The invention provides a preparation method of trifloxystrobin characteristic impurities, which comprises the following steps: (1) carrying out saponification reaction on trifloxystrobin and alkali to obtain trifloxystrobin salt; and (2) carrying out condensation reaction on the trifloxystrobin salt and bromo-oxime ether, and carrying out post-treatment on a generated crude product to obtain the trifloxystrobin characteristic impurity. According to the preparation method, the trifloxystrobin characteristic impurities are rapidly synthesized through saponification and condensation, the process steps are simple, the reaction conditions are mild, operation is easy, the raw material conversion rate is high, and no side reaction occurs; wherein the purity of the final product obtained through post-treatment is greater than 98.5%, and the yield can reach 87% or above. The trifloxystrobin characteristic impurity obtained by the preparation method provided by the invention has the characteristics of high purity and high yield, and can be used as a reference substance. The technology is beneficial to development of a trifloxystrobin analysis method and more beneficial to quality control of trifloxystrobin, and a new idea is provided for product quality control.

Description

Technical field [0001] The invention belongs to the technical field of organic compound preparation, and specifically relates to a method for preparing trifloxystrobin characteristic impurities. Background technique [0002] Trifloxystrobin is a second-generation methoxyacrylate fungicide developed by Syngenta and Bayer of Germany. It has the advantages of broad spectrum, good resistance to rain erosion, long duration of effect, and safety to crops. , safe for crops, its structural formula is as follows: [0003] [0004] Since trifloxystrobin can be rapidly degraded in soil and water, it is highly safe for the environment. Moreover, trifloxystrobin is a fungicide with chemical kinetic properties. It can be strongly adsorbed by the plant wax layer and provide excellent protection to the plant surface. protective activity. Suitable crops for trifloxystrobin include wheat, barley, rye, triticale, grapes, apples, peanuts, bananas and vegetables, etc., with a wide range of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C249/12C07C251/60
CPCC07C249/12C07C251/60
Inventor 张荣黄超群罗亮明朱锦涛向顺
Owner 长沙嘉桥生物科技有限公司
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