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13 c-labeled pyraclostrobin and its synthesis method

A pyraclostrobin and labeling technology is applied in the direction of organic chemical methods, chemical instruments and methods, and fungicides. It can solve the problems of many impurities, complex synthesis processes, and difficult purification, and achieves easy separation and purification, simple operation process, and Effect of High Atom Utilization

Active Publication Date: 2020-03-27
河南衡谱分析检测技术有限公司
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Problems solved by technology

[0008] The first object of the present invention is to provide a 13 Synthesis method of C-labeled pyraclostrobin to alleviate the technical problems existing in the prior art that the isotope-labeled pyraclostrobin synthesis process is complicated, the impurities are many, the yield is low, the purification is difficult, and it cannot be mass-produced

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  • <sup>13</sup> c-labeled pyraclostrobin and its synthesis method
  • <sup>13</sup> c-labeled pyraclostrobin and its synthesis method
  • <sup>13</sup> c-labeled pyraclostrobin and its synthesis method

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preparation example Construction

[0039] The present invention provides a 13 The synthetic method of the pyraclostrobin of C mark, comprises the steps:

[0040] Step (a): using chlorobenzene as a raw material to obtain the first product through acylation reaction and condensation ring closure reaction;

[0041] Step (b): methyl o-toluene acetate undergoes condensation reaction, methylation reaction and bromination reaction to obtain the second product;

[0042] Step (c): the first product and the second product are reacted in an alkaline environment to obtain 13 C-labeled pyraclostrobin.

[0043] Among them, the stable isotope 13 The C label is introduced by one or more of the acylation reaction in step (a), the condensation reaction in step (b), or the methylation reaction, such as a single-site stable isotope 13 The C label can be introduced by acylation in step (a), by condensation in step (b), or by methylation in step (b); stable isotopes at both sites 13 The C label can be introduced by an acylation r...

Embodiment 1

[0091] This embodiment provides a 13 A preparation method for C-labeled pyraclostrobin, the method comprising the following steps:

[0092] (1) Preparation of 3-(4-chlorophenyl)-1-methyl-1H-5-pyrazolol (I-5)

[0093] Under the protection of nitrogen, aluminum trichloride (5.10g, 7.58mmol) and chlorobenzene (7.0mL, 69.40mmol) were added to a 150mL stuffy jar, and added by syringe at room temperature 13 C-labeled acetyl chloride (5.0 g, 62.89 mmol) was post-blocked and stirred at 55 °C for 6 h. After cooling, the reaction solution was quenched in ice water, extracted, and concentrated to obtain p-chloroacetophenone (8.90 g, yield 82.40%) as light yellow oil. The tetrahydrofuran (50mL) solution of p-chloroacetophenone (5.26g, 33.72mmol) was respectively charged into the three-necked flask protected by nitrogen, and NaHMDS (2M in THF, 25.3mL, 50.58mmol) was added under the ice-salt bath and stirred for 0.5h, and then Dimethyl carbonate (3.1 mL, 37.09 mmol) was added and the mix...

Embodiment 2

[0099] 13 A preparation method for C-labeled pyraclostrobin, the method comprising the following steps:

[0100] (1) Preparation of 3-(4-chlorophenyl)-1-methyl-1H-5-pyrazolol (I-5)

[0101] Under the protection of nitrogen, aluminum trichloride (5.10g, 7.58mmol) and chlorobenzene (7.0mL, 69.4mmol) were added in a 150mL stuffy jar, and acetyl chloride (5.00g, 62.89mmol) was added through a syringe at room temperature to seal, And stirred at 55°C for 6h. After cooling, the reaction solution was quenched in ice water, extracted, and concentrated to obtain p-chloroacetophenone (8.9 g, yield 82.4%) as light yellow oil. NaH (60%, 2.72g, 68.12mmol), tetrahydrofuran (50mL) and dimethyl carbonate (3.1mL, 37.09mmol) were respectively charged into a three-neck flask protected by nitrogen. The mixture was heated to reflux and stirred for 30 min, then a tetrahydrofuran solution of p-chloroacetophenone (5.26 g, 33.72 mmol) was added dropwise within 15 min, continued to stir for 6 h and t...

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Abstract

The invention provides <13>C marked pyraoxystrobin and a synthetic method thereof, and relates to the technical field of stable isotope labelling synthesis. The synthetic method of the <13>C marked pyraoxystrobin provided by the invention comprises the steps that chlorobenzene is used as a raw material; through acylation reaction and condensation cyclization reaction, a first product is obtained;O-methylphenylacetic acid methyl ester is subjected to condensation reaction, methylation reaction and bromination reagent reaction to obtain a second product; the first product and the second productreact in alkaline environment to obtain the <13>C marked pyraoxystrobin. The operation process of the synthetic method provided by the invention is simple; the stable isotope atom utilization rate ishigh. The <13>C marked pyraoxystrobin synthetized by the synthetic method provided by the invention has the advantages that the separation and the purification are easy; the product chemical purity reaches 98 percent or higher; the isotope abundance is 98 percent or higher.

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. 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 inhibi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/20C07B59/00A01P3/00G01N1/28
CPCC07B59/002C07B2200/05C07D231/20G01N1/28
Inventor 贾明宏
Owner 河南衡谱分析检测技术有限公司
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