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Metalaxyl synthesizing process

A technology of metalaxyl and dimethylphenyl, which is applied in the field of synthesis of bactericidal active compounds, can solve the problems of many side reactions, long time, high temperature, etc., achieve improved conversion rate, low reaction temperature, and overcome racemization The effect of action

Inactive Publication Date: 2007-12-19
DAQING PETROLEUM ADMINISTRATION
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

It is difficult to carry out the reaction in the last step of synthesis, requiring higher temperature and longer time, and more side reactions

Method used

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  • Metalaxyl synthesizing process

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Embodiment 1

[0008] Embodiment 1, under the protection of nitrogen, add 24.2 grams (0.2 moles) 2,6-dimethylaniline, 25.2 grams (0.3 moles) sodium bicarbonate and 50 grams (0.3 moles) 2-bromopropionic acid methyl in the reaction flask respectively ester. Under stirring, the temperature was slowly raised to 120-125°C within one hour, maintained at this temperature for 18 hours and then cooled. The reaction mixture was poured into 300 ml of ice water, extracted with ethyl acetate, and the extract was dried over anhydrous sodium sulfate. Concentrated by rotary evaporation at 40°C to obtain the crude ester, which was purified by distillation to obtain 26 g of methyl 2-(2,6-dimethylphenyl)alanine, with a yield of 63%.

[0009] Add 20.7 grams (0.1 moles) of 2-(2,6-dimethylphenyl) methyl aminopropionate, 0.61 grams (0.005 moles) of 4-dimethylaminopyridine (DMAP), and 50 milliliters of toluene in the reaction flask , 10.1 grams (0.1 moles) of triethylamine, stirring and adding dropwise 11.9 grams...

Embodiment 2

[0010] Example 2, 207 grams (1 mole) of 2-(2,6-dimethylphenyl) methyl-alanine, 6.1 grams (0.05 mole) of 4-dimethylaminopyridine, pyridine 79 gram (1 mole), 600 milliliters of dichloromethane, 108.5 grams (1 mole) of methoxyacetyl chloride was added dropwise with stirring at room temperature, and the reaction temperature rose to 40 ° C. After the dropwise addition, the reaction temperature was gradually reduced to room temperature. The reaction was stopped, washed with water, extracted with 100 ml of dichloromethane, and concentrated to obtain 255 grams of metalaxyl, with a liquid chromatography purity of 90% and a yield of 82% (using 2-(2,6-dimethylphenyl)aminopropionic acid methyl ester meter). Liquid chromatography analysis conditions: C18 column (250mm×4mm), mobile phase: methanol+water=70+30(v / v), flow rate 1.0mL / min, detection wavelength 220nm, metalaxyl retention time 5.8min, area Normalized quantification.

Embodiment 3

[0011] Embodiment 3, add 207 grams (1 mole) 2-(2,6-dimethylphenyl) methyl-alanine respectively, 0.12 grams (0.01 moles) 4-dimethylaminopyridine, anhydrous Potassium carbonate 276 grams (2 moles), dichloroethane 600 milliliters, stirring and dropping 119 grams (1.1 moles) methoxyacetyl chloride at room temperature, reaction temperature is maintained at 120~140 ℃, stop reaction after 1 hour, wash with water, 100 ml of dichloromethane was extracted and concentrated to obtain 255 g of metalaxyl, with a liquid chromatography purity of 90% and a yield of 82% (based on methyl 2-(2,6-dimethylphenyl)alanine). Liquid chromatography analysis conditions: C18 column (250mm×4mm), mobile phase: methanol+water=70+30(v / v), flow rate 1.0 mL / min, detection wavelength 220nm, retention time of metalaxyl 5.8min, area Normalized quantification.

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Abstract

The metalaxyl synthesizing process includes the following steps: the reaction of 2-(2, 6-dimethyl phenyl) methyl alanine, alkali and catalyst 4-dimethylin pyridine in the molar ratio of 1 to 1-2 to 0.01-0.1 and dissolved in proper solvent; dropping methoxyl acetyl chloride to react for 1-4 hr, with the molar ratio between 2-(2, 6-dimethyl phenyl) methyl alanine and methoxyl acetyl chloride being 1 to 1-1.5; water washing the resultant, ether extraction and concentrating to obtain metalaxyl. The process has the features of mild reaction condition, high yield, less side reactions and short reaction period.

Description

Technical field: [0001] The invention relates to a method for synthesizing bactericidal active compounds, in particular to a method for synthesizing metalaxyl at room temperature. Background technique: [0002] Metalaxyl is a fungicide widely used at present. Its synthesis methods include lactic acid method, high-pressure hydrogenation method and halogenated propionate method. Among them, the halogenated propionate method uses 2,6-dimethylaniline as the starting material , react with methyl α-chloro or bromopropionate to synthesize methyl 2-(2,6-dimethylphenyl)aminopropionate, and then 2-(2,6-dimethylphenyl)amino Metalaxyl was synthesized by reacting methyl propionate and methoxyacetyl chloride in the presence of sodium bicarbonate at 110°C for 6 hours. It is difficult to carry out the reaction in the last step of synthesis, requiring higher temperature and longer time, and there are many side reactions. Invention content: [0003] In order to overcome the shortcomings o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/02C07C233/47
Inventor 郑良玉张锁秦解永成丁智勇朱雪峰
Owner DAQING PETROLEUM ADMINISTRATION
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