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Synthesis method of S-metolachlor

A technology for the synthesis of refined metolachlor and its synthesis method, which is applied in the field of synthesizing refined metolachlor, and can solve the problems that the technology is still blank

Inactive Publication Date: 2011-04-13
江苏常隆化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The current synthesis method used for industrialization is mainly asymmetric catalytic hydrogenation used abroad, but the technology used for industrialization in China is still blank

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] In a 500 ml three-necked flask, add 300 ml of dichloromethane, then add 63.0 g (0.55 moles) of methanesulfonyl chloride, and 59.1 g (0.50 moles) of (D)-ethyl lactate into the reaction flask, and dropwise add triethyl 55.5 g (0.55 mol) of amine, temperature controlled in ice-water bath -10°C to -5°C, follow the reaction (D)-ethyl lactate to complete the reaction, filter, wash the filtrate with 45 ml of water, separate layers, and wash the water layer with 45 ml of dichloro Extracted with methane, combined the organic layers, dried with 20 g of anhydrous sodium sulfate, filtered, and spin-dried the solvent to obtain 88.3 g of (R)-2-(methylsulfonyloxy)propionate, with a yield of 90%. Put 71.5 grams (0.53 moles) of 2-methyl-6-ethylaniline and 98.1 grams (0.50 mol), heat up to 120°C, slowly add 41.87 g (0.53 mol) of pyridine dropwise, continue to heat up to 130°C after dropping, keep warm for 1 hour, cool to room temperature, pour the reaction solution into 260 ml of ice wat...

Embodiment 2

[0018] In a 500 ml three-neck flask, add 300 ml of tetrahydrofuran, then add 63.0 g (0.55 moles) of methanesulfonyl chloride, and 59.1 g (0.50 moles) of (D)-ethyl lactate into the reaction flask, and control the temperature in an ice-water bath at 0°C , dropwise added 55.5 g (0.55 moles) of triethylamine, followed by chromatographic tracking of the reaction (D)-ethyl lactate was completely reacted, filtered, and after the solvent was removed under reduced pressure, the product was obtained by distillation under vacuum conditions, (R)-2-( Methanesulfonyloxy) propionate 88.9 grams, the yield is 91%.

[0019] Put 71.5 grams (0.53 moles) of 2-methyl-6-ethylaniline and 98.1 grams (0.50 mol), heat up to 120°C, slowly add 41.87 g (0.53 mol) of pyridine dropwise, continue to heat up to 130°C after dropping, keep warm for 1 hour, cool to room temperature, pour the reaction solution into 260 ml of ice water, stir for 30 minutes, And add water to wash until neutral, the aqueous layer is...

Embodiment 3

[0024]In a 500 ml three-necked flask, add 300 ml of tetrahydrofuran, then add 63.0 g (0.55 moles) of methanesulfonyl chloride, and 52.1 g (0.50 moles) of (D)-methyl lactate into the reaction flask, and control the temperature in an ice-water bath at 0°C , 75.9 grams (0.55 moles) of potassium carbonate was added dropwise, and the reaction (D)-ethyl lactate was completely reacted by chromatography, filtered, and the solvent was removed under reduced pressure, and the product was obtained by distillation under vacuum conditions, (R)-2-(form Sulfonyloxy) propionate 86 grams, yield is 88%.

[0025] Put 71.5 grams (0.53 moles) of 2-methyl-6-ethylaniline and 98.1 grams (0.50 mol), heat up to 120°C, slowly add 41.87 g (0.53 mol) of pyridine dropwise, continue to heat up to 130°C after dropping, keep warm for 1 hour, cool to room temperature, pour the reaction solution into 260 ml of ice water, stir for 30 minutes, And add water to wash until neutral, the aqueous layer is extracted wi...

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PUM

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Abstract

The invention discloses a synthesis method of S-metolachlor, comprising the following steps: 1) reacting (R)-methyl lactate or (R)-ethyl lactate with methanesulfonyl chloride to generate (R)-2-(mesyloxy)propionate; 2) reacting the obtained (R)-2-(mesyloxy)propionate with 2-methyl-6-ethylphenylamine to obtain (S)-N-(2-methyl-6-ethyl phenyl) phenylalanine ester; 3) reducing an ester group into corresponding alcohol by a reducing agent; 4) obtaining acyamino alcohol by performing acylation on the alcohol and chloroacetic chloride; and 5) obtaining the S-metolachlor through methylation reaction. The S-metolachlor produced by the synthesis method is low in production cost and good in optical purity, the ee value reaches 90-93%, and the yield is up to 86-89%. The synthesis method is simple to operate and easy to realize industrialization.

Description

technical field [0001] The invention relates to a method for synthesizing refined metolachlor. technical background [0002] Jindul (Mepromet) is a new generation of high-tech product developed by Swiss Syngenta on the basis of the world's largest selective herbicide-Dur, and it is a class of chloroacetylchloramine compounds. However, compared with traditional chloroacetyl chloramine compounds, it is an optically active compound, that is to say, it is a class of chiral pesticides. In recent years, chirality has emerged as a key factor in life sciences. Chiral pesticides have attracted widespread attention. The main reason is that in racemic pesticides, the two enantiomers that make up the racemate have different effects on biological activity and can be separated to make the best use of them. Because in one enantiomer, its biological activity usually exists in one of the enantiomers, the biggest advantages of chiral pesticides are lower residues, higher drug efficacy, and ...

Claims

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Application Information

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IPC IPC(8): C07C233/88C07C231/12
Inventor 陆明若王俊科张中泽田庆海杨春华刘梅
Owner 江苏常隆化工有限公司
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