Unsaturated oxime ether compound preparation method

A technology of ether compounds and compounds, applied in oxime preparation, organic chemistry, etc., can solve the problems of complex post-processing and restrictions on industrial production, and achieve the effects of simple post-processing, easy industrial production, and increased reaction yield

Active Publication Date: 2018-06-22
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The total yield of the two-step reaction is only 22.07%, and the post-treatment is complicated, which seriously limits the industrial production of this type of product

Method used

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  • Unsaturated oxime ether compound preparation method
  • Unsaturated oxime ether compound preparation method
  • Unsaturated oxime ether compound preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Methoxyimino-N-methyl-2-[[[[[[4-(2,6-dimethyl)phenyl]-3-buten-2-yl]imino]oxy]methyl ] Synthesis of phenylacetamide

[0025]

[0026] Add (E)-2-(bromomethyl)-α-methoxyiminophenylacetic acid methyl ester (75.5g, 0.2mol), acetone (390g), 2,6-dichlorostyryl Methyl ketoxime (46.1 g, 0.20 mol) and potassium carbonate (44.6 g, 0.32 mol) were heated up to 58°C and kept at reflux for 5 hours. After the reaction is over, the water bath is heated at 80°C under normal pressure to recover acetone until there is basically no distillate, and the precipitation is stopped. Add dichloromethane (350mL) and 150g of water, stir until completely dissolved, then let stand for stratification, separate the organic phase and wash it with water (150g) once, after separating the washed organic phase, heat it in a water bath at 70°C and distill it to the basic Continue depressurizing for 10 min after no fractions, then stop, add methanol (122g) after cooling down slightly, heat up and reflux u...

Embodiment 2

[0030] Methoxyimino-N-methyl-2-[[[[[[4-(2,6-dimethyl)phenyl]-3-buten-2-yl]imino]oxy]methyl ] Synthesis of phenylacetamide (solvent butanone)

[0031]

[0032] Add (E)-2-(bromomethyl)-α-methoxyiminophenylacetic acid methyl ester (75.5g, 0.2mol), methyl ethyl ketone (350g), 2,6-dichlorostyrene to the reaction flask in sequence Methyl ketoxime (46.1g, 0.2mol) and potassium carbonate (41.4g, 0.30mol) were heated to 60°C and kept for 4h. After the reaction is over, the butanone is recovered under reduced pressure in a water bath until there is basically no distillate, and the precipitation is stopped. Add dichloromethane (350mL) and 150g of water, stir until completely dissolved, then let stand for stratification, separate the organic phase and wash it with water (150g) once, after separating the washed organic phase, heat it in a water bath at 70°C and distill it to the basic Continue depressurizing for 10 minutes after no fractions, stop, add methanol (122g) after cooling do...

Embodiment 3

[0036] Methoxyimino-N-methyl-2-[[[[[[4-(2,6-dimethyl)phenyl]-3-buten-2-yl]imino]oxy]methyl ] Synthesis of phenylacetamide

[0037]

[0038]Add (E)-2-(bromomethyl)-α-methoxyiminophenylacetic acid methyl ester (75.5g, 0.2mol), acetone (390g), 2,6-dichlorostyryl Methyl ketoxime (46.1 g, 0.20 mol) and cesium carbonate (97.7 g, 0.30 mol) were heated up to 58° C. and refluxed for 4 hours. After the reaction is over, the water bath is heated at 80°C under normal pressure to recover acetone until there is basically no distillate, and the precipitation is stopped. Add dichloromethane (350mL) and 150g of water, stir until completely dissolved, then let stand for stratification, separate the organic phase and wash it with water (150g) once, after separating the washed organic phase, heat it in a water bath at 70°C and distill it to the basic Continue depressurizing for 10 minutes to stop after no fraction, add methanol (122g) after cooling down slightly, heat up and reflux until the...

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PUM

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Abstract

The invention relates to an unsaturated oxime ether compound (I) preparation method, wherein the reaction formula is defined in the specification, and each group in the formula is defined in the specification. According to the present invention, with the method, styryl methyl ketone oxime (II) and bromo oxime ether (III) are subjected to a reaction in a ketone solvent by using a carbonate as an alkali to prepare a high-yield oxime ether compound (IV), and further the unsaturated oxime ether compound (I) is prepared through aminolysis under the action of methylamine.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for preparing unsaturated oxime ether compounds. Background technique [0002] Unsaturated oxime ether compounds are a class of compounds with high fungicidal activity. Compound-methoxyimino-N-methyl-2-[[[[[[4-(2,6-dimethyl)phenyl]-3-buten-2-yl]imino is disclosed in CN1309897A ]oxyl]methyl]phenylacetamide (compound number: 1), biological activity studies have shown that this compound has the characteristics of broad bactericidal spectrum, high bactericidal activity, and both therapeutic and protective effects, and has been commercially developed. The common name is Enoxastrobin. [0003] [0004] Although the preparation method of unsaturated oxime ether compounds is disclosed in CN1309897A: styryl methyl ketone oxime and (E)-2-(bromomethyl)-alpha-methoxyiminophenylacetic acid methyl ester in alkaline The condensation reaction is carried out under the c...

Claims

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Application Information

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IPC IPC(8): C07C249/04C07C249/12C07C251/60
CPCC07C249/04C07C249/12C07C251/60
Inventor 于海波吴长春任忠宝张则勇王风儒董燕吴鸿飞
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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