Method for preparing bactericidal agent intermediate (E)-2-(2'-chloromethyl)phenyl-2-methoxy imino methyl acetate

A technology of methyl methoxyiminoacetate and o-methylol benzoic acid lactone is applied in the field of preparation of formula intermediates, and can solve the problem of device blockage, unsuitability, and interference with distillation and purification of o-chloromethyl benzoyl chloride and other problems to achieve the effect of improved safety, high yield and reduced risk

Active Publication Date: 2008-03-12
JIANGSU GENGYUN CHEM CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Quaternary ammonium salts have sublimation effect, which will cause device blockage, and quaternary ammonium salts can also interfere with the distillation purification of o-chloromethylbenzoyl chloride
[0006] What patent CN1037175 reported was the synthesis method of the product o-chloromethylbenzoyl cyanide of step 2) of the present invention. The shortcoming of this method is that it is necessary to add 1% hydrochloric acid to adjust the pH value of the reactio

Method used

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  • Method for preparing bactericidal agent intermediate (E)-2-(2'-chloromethyl)phenyl-2-methoxy imino methyl acetate
  • Method for preparing bactericidal agent intermediate (E)-2-(2'-chloromethyl)phenyl-2-methoxy imino methyl acetate
  • Method for preparing bactericidal agent intermediate (E)-2-(2'-chloromethyl)phenyl-2-methoxy imino methyl acetate

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Effect test

Embodiment 1

[0039] Embodiment 1, the preparation method of agricultural fungicide chemical intermediate (E)-2-(2'-chloromethyl)phenyl-2-methoxyiminoacetic acid methyl ester, with reference to Fig. 1:

[0040] Step 1, the preparation of o-chloromethylbenzoyl chloride

[0041] 271g (99%, 2.0mol) o-hydroxymethylbenzoic acid lactone (phthalide), 10.5g (99%, 0.1mol) trimethyl borate, 28.5g (99% 0.1mol) triphenylphosphine oxide were added to In a 500ml reaction flask, heat it to 130°C under stirring, and add 324.5g (99%, 2.7mol) of thionyl chloride dropwise to the reaction flask for 3 to 5 hours. After the addition is complete, the mixture is reacted at 130°C for 5 hours. The reaction effluent was distilled under reduced pressure to obtain 366.4 g of the product; the purity was 98% (GC), and the yield was 95%.

[0042] Step 2, the preparation of o-chloromethyl benzoyl cyanide

[0043]Add 120g (98%, 2.4mol) of sodium cyanide and 470ml of water into a 3000ml reaction flask, dissolve the sodium ...

Embodiment 2

[0050] Embodiment 2 is basically the same as Embodiment 1, but has the following changes:

[0051] Step 1, the preparation of o-chloromethylbenzoyl chloride

[0052] Add 271g (99%, 2.0mol) o-hydroxymethylbenzoic acid lactone (phthalide), 3.8g (99%, 0.06mol) boric acid, 17g (99%, 0.06mol) triphenylphosphine oxide to a 500ml reaction bottle 324.5 g (99%, 2.7 mol) of thionyl chloride was added dropwise to the reaction flask in 3 to 5 hours, and after the addition was completed, the mixture was reacted at 130°C for another 5 hours, and the reaction discharge Distillation under reduced pressure gave 366 g of the product; the purity was 97% (GC), and the yield was 94%.

[0053] Step 2, the preparation of o-chloromethyl benzoyl cyanide

[0054] Add 162.5g (96%, 2.4mol) of potassium cyanide and 460ml of water into a 3000ml reaction flask, dissolve potassium cyanide into an aqueous solution under stirring, then add 1544g of toluene, 23g (99%, 0.1mol) of benzyl trichloride Ethyl ammo...

Embodiment 3

[0055] Embodiment 3 is basically the same as Embodiment 1, but has the following changes:

[0056] Step 1, the preparation of o-chloromethylbenzoyl chloride

[0057] 271g (99%, 2.0mol) o-hydroxymethylbenzoic acid lactone (phthalide), 10.5g (99%, 0.1mol) trimethyl borate, 26.5g (99%, 0.1mol) triphenylphosphine were added to In a 500ml reaction flask, heat it to 130°C under stirring, and add 324.5g (99%, 2.7mol) of thionyl chloride dropwise to the reaction flask for 3 to 5 hours. After the addition is complete, the mixture is reacted at 130°C for 5 hours. The reaction effluent was distilled under reduced pressure to obtain 370.5 g of the product; the purity was 97% (GC), and the yield was 95%.

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Abstract

The preparation method of the fungicide intermediate (E)-2-(2'-chloromethyl)-2-methicillin imino acetic methyl ester is: 1) the phenyl phthalate and the thionyl dihalide react with the influence of a catalyst; the catalyst is the Louis acid and phosphonic derivative; 2) the product of the first step and the alkali metal cyanide react with the influence of the organic solvent and phase transfer catalyst; the organic solvent is selected from the non-polar aromatic solvent or the halogen hydrocarbon; the phase transfer catalyst is selected from the halide of the four-level nitride or the ammonium salt; the alkali metal cyanide is selected from the sodium cyanide and potassium cyanide; 3) the products of the second step and the methanol react under the condition with the organic solvent and the chlorinated hydrogen; 4) the products of the third step and the methicillin amine hydrochloride under the condition with the organic solvent; thus, the target product can be got. The energy consumption and production risk of the present invention are obviously lowered; the relative collection rate is high; the safety in the production process is improved; and the present invention has no drawbacks such as the obstruction.

Description

technical field [0001] The present invention relates to a kind of preparation method of formula (I) intermediate, be specifically related to a kind of (E)-2- The preparation method of (2'-chloromethyl)phenyl-2-methoxyiminoacetic acid methyl ester. Background technique [0002] The compound involved in this application is an intermediate (E)-2-(2'-chloromethyl)phenyl-2-methoxyiminoacetic acid methyl in the preparation process of fungicidal methoxyacrylate derivatives Ester, namely the compound shown in formula (I). Related to the preparation method of this compound in the prior art, there are the following related schemes. [0003] What patent DE 2835440 discloses is the synthetic method of the product o-chloromethylbenzoyl chloride of step 1) of the present invention, is to use corresponding methyl to replace benzoyl chloride and chlorine halogenation reaction, obtain product through rectification again, the shortcoming of this method Because the reaction can only generat...

Claims

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Application Information

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IPC IPC(8): C07C251/48C07C249/08A01N37/50A01P3/00
Inventor 于康平李泽方张少华罗志会
Owner JIANGSU GENGYUN CHEM CO LTD
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