13C-labelled pyraoxystrobin and synthesis method thereof

A synthetic method, the technology of pyraclostrobin, applied in the field of stable isotope labeling synthesis, can solve the problems of many impurities, complex synthesis process, and difficult purification, and achieve the effect of easy separation and purification, simple operation process, and high atom utilization rate

Inactive Publication Date: 2018-01-26
贾明宏
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Problems solved by technology

[0008] The first object of the present invention is to provide a 13 A synthetic method for C-labeled pyraclostrobin to alleviate the technical problems of isotope-labeled pyraclostrobin synthesis process complex, many impurities, low yield, difficult purification, and incapable of batch production in the prior art

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  • 13C-labelled pyraoxystrobin and synthesis method thereof
  • 13C-labelled pyraoxystrobin and synthesis method thereof

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[0035] The present invention provides a 13 The synthetic method of the pyraclostrobin of C mark, comprises the steps:

[0036] Step (a): Using stable isotopes 13 The chlorobenzene of C mark is raw material, obtains the first product through acylation reaction, condensation ring reaction;

[0037] Step (b): Methyl o-toluene acetate undergoes condensation reaction, methylation reaction and bromination reaction to obtain the second product;

[0038]Step (c): the first product and the second product are reacted in an alkaline environment to obtain 13 C-labeled pyraclostrobin.

[0039] The synthesis method provided by the invention has simple operation process and high utilization rate of stable isotope atoms.

[0040] In a preferred embodiment, the acylation reaction in step (a) comprises acetylation reaction and formylation reaction;

[0041] The reagent of acetylation reaction is acetyl chloride; The reagent of formylation reaction is selected from dimethyl carbonate or met...

Embodiment 1

[0098] This embodiment provides a 13 C 7 A preparation method for marking pyraclostrobin, the method comprising the following steps:

[0099] (1) Preparation of 3-(4-chlorophenyl)-1-methyl-1H-5-pyrazolol (I-5)

[0100] Under nitrogen protection, aluminum trichloride (0.510g, 0.758mmol) and 13 C 6 Labeled chlorobenzene (0.7mL, 6.940mmol) was added to a 10mL stuffy jar, and acetyl chloride (0.500g, 6.289mmol) was added via a syringe at room temperature to seal it, and stirred at 55°C for 6h. After cooling, the reaction solution was quenched in ice water, extracted, and concentrated to obtain p-chloroacetophenone (0.890 g, yield 82.40%) as pale yellow oil. A three-necked flask protected by nitrogen was respectively charged with a tetrahydrofuran (10 mL) solution of p-chloroacetophenone (0.526 g, 3.372 mmol), and NaHMDS (2M in THF, 2.5 mL, 5.058 mmol) was added under an ice-salt bath and stirred for 0.5 h, and then Dimethyl carbonate (0.3 mL, 3.709 mmol) was added and the mix...

Embodiment 2

[0106] 13 C 7 A method for preparing pyraclostrobin, the method comprising the following steps:

[0107] (1) Preparation of 3-(4-chlorophenyl)-1-methyl-1H-5-pyrazolol (I-5)

[0108] Under nitrogen protection, aluminum trichloride (0.510g, 0.758mmol) and 13 C 6 Labeled chlorobenzene (0.7mL, 6.940mmol) was added to a 10mL stuffy jar, and acetyl chloride (0.500g, 6.289mmol) was added via a syringe at room temperature to seal it, and stirred at 55°C for 6h. After cooling, the reaction solution was quenched in ice water, extracted, and concentrated to obtain p-chloroacetophenone (0.890 g, yield 82.4%) as pale yellow oil. NaH (60%, 0.272g, 6.812mmol), tetrahydrofuran (10.0mL) and dimethyl carbonate (0.3mL, 3.709mmol) were respectively charged into a three-necked flask protected by nitrogen. The mixture was heated to reflux and stirred for 0.5 h, then a tetrahydrofuran solution (2.0 mL) of p-chloroacetophenone (0.526 g, 3.372 mmol) was added dropwise within 15 minutes, stirring ...

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Abstract

The invention provides 13C-labelled pyraoxystrobin and a synthesis method thereof and relates to the technical field of stable isotope labeling synthesis. The provided synthesis method of the 13C-labelled pyraoxystrobin comprises steps as follows: stable isotope 13C-labelled chlorobenzene is taken as a raw material and subjected to an acylation reaction and condensation loop closing, and a first product is obtained; methyl o-tolylacetate is subjected to a condensation reaction, a methylation reaction and a reaction with a bromination reagent, and a second product is obtained; the first productand the second product react in an alkaline environment, and 13C-labelled pyraoxystrobin is obtained. The provided synthesis method is simple in operation process, the utilization rate of stable isotope atoms is high, the 13C-labelled pyraoxystrobin synthesized with the provided synthesis method is easy to separate and purify, the chemical purity of the product is 98% or above, and the isotope abundance is 98% or above.

Description

technical field [0001] The invention relates to the technical field of stable isotope labeling synthesis, in particular to a 13 C-labeled pyraclostrobin and its synthesis method. Background technique [0002] Pyraoxystrobin (pyraoxystrobin), the chemical name is (E)-2-[2-[[3-(4-chlorophenyl)-1-methyl-1H-pyrazole-5-oxyl]methyl]benzene Base]-3-methoxymethyl acrylate, the English chemical name is (E)-2-[[[3-(4-chlorophenyl)-1-methyl-1H-pyrazol-5-yl]oxy]methyl]- α-(methoxymethylene)-methyl ester. Molecular formula: C 22 h 21 ClN 2 o 4 , CAS accession number is 862588-11-2. [0003] Pyclostrobin is a methoxyacrylate fungicide, created and developed by Shenyang Research Institute of Chemical Industry. The drug is a respiratory inhibitor of fungal mitochondria, and its mechanism of action is to block the electron transfer between cytochrome b and cl, prevent cellular energy synthesis, and inhibit mitochondrial respiration to achieve bactericidal effect. Pyclostrobin can in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/20
Inventor 贾明宏
Owner 贾明宏
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