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Preparation process of safe herbicide preparation of n-dichloroacetyl oxazolidine herbicide

A technology of dichloroacetyl oxazolidine and dichloroacetyl chloride is applied in the synthesis field of herbicide safener, can solve the problems of high reaction conditions, long reaction time, complicated operation and the like, and achieves mild reaction conditions and high reaction time. The effect of short, high promotion value

Inactive Publication Date: 2009-08-12
NORTHEAST AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this method is that the reaction time is long, the operation is complicated, the reaction temperature is high, the by-product is high with triethylamine as the acid-binding agent, the yield is low, and the cost is high
At present, there is no patent on the synthesis method of dichloroacetyl oxazolidine compounds in China, only the preparation method of oxazolidine (CN200410012505.6), but the reaction conditions are still higher than the conditions of this method, the method is complicated, and the reaction time is long

Method used

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  • Preparation process of safe herbicide preparation of n-dichloroacetyl oxazolidine herbicide
  • Preparation process of safe herbicide preparation of n-dichloroacetyl oxazolidine herbicide

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Experimental program
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Effect test

Embodiment 1

[0026] Add 0.067mol 2-methyl-2-aminopropanol, 0.067mol n-butyraldehyde, and 20.0mL chloroform into a three-necked flask. The three-necked flask is equipped with a thermometer, a reflux condenser and a dropping funnel, and the temperature is controlled at 33-34 Stir at ℃ for 1 hr, reflux for about 1.5 h, cool to -10 ℃, add 7.5 mL of 33% NaOH solution, add dichloroacetyl chloride dropwise, control the rate of addition, and control the temperature of the reaction system in the range of -10 to 0 ℃, After the dropwise addition, the organic phase was washed with water until neutral, and the organic phase was dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the crude product was recrystallized from cyclohexane to obtain compound I in a yield of 58.2%.

Embodiment approach 2

[0028] Add 0.067mol 2-methyl-2-aminopropanol, 0.067mol paraformaldehyde, 1.5mL water, and 20.0mL chloroform into a three-necked flask. The three-necked flask is equipped with a thermometer, a reflux condenser and a dropping funnel to control the temperature. Stir for 1 hr at 33-34 °C, reflux for about 1.5 h, cool to -10 °C, add 7.5 mL of 33% NaOH solution, add dichloroacetyl chloride dropwise, control the rate of addition, and control the temperature of the reaction system at -10-0 °C Within the range, after the dropwise addition, the organic phase was washed with water until neutral, and the organic phase was dried with anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, the crude product was separated by silica gel column chromatography, and the solvent was evaporated under reduced pressure to obtain white crystals to obtain compound II in a yield of 60.4%.

Embodiment approach 3

[0030] Add 0.067mol 2-methyl-2-aminopropanol, 0.067mol cyclopentanone, and 20.0mL chloroform to a three-necked flask, the three-necked flask is equipped with a thermometer, a reflux condenser and a dropping funnel, and the temperature is controlled at 33-34 Stir at ℃ for 1 hr, reflux for about 1.5 h, cool to -10 ℃, add 7.5 mL of 33% NaOH solution, add dichloroacetyl chloride dropwise, control the rate of addition, and control the temperature of the reaction system in the range of -10 to 0 ℃, A small amount of NaOH solution was added to maintain the pH value of the reaction system above 12. After the dropwise addition, the organic phase was washed with water until neutral, and the organic phase was dried with anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, the crude product was separated by silica gel column chromatography, the solvent was evaporated under reduced pressure, and then recrystallized with cyclohexane to obtain white...

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Abstract

The present invention provides preparation process of new N-dichloroacetyl-1, 3-oxazolidine compound. The preparation process includes the following steps: 1. dissolving 2-methyl-2-amino propanol and aldehyde or ketone of different structure in the molar ratio of 1 to 1-1 to 1.5 in solvent; 2. stirring at 33-38 deg.c, refluxing and separating out water, cooling the reaction system to -10 deg.c, adding acid-binding agent, and dropping dichloroacetyl chloride slowly to maintain the pH value of the reaction system in over 12; 3. washing the organic phase with water to neutrality, drying with anhydrous magnesium sulfate and distilling off solvent; and 4. adding solvent to re-crystallize or column chromatography to separate so as to obtain white crystal. Compared with available technology, the present invention has the advantages of mild reaction cn, short reaction period, less side products and high yield.

Description

technical field [0001] The invention relates to the research field of organic synthesis and pesticide synthesis, in particular to a synthesis method of a herbicide safener. Background technique [0002] Dichloroacetyloxazolidines It is a new type of herbicide safener, a good antidote for chloroacetanilide and thiocarbamate herbicides, and can be used as sulfonylurea and imidazolinone herbicides in grass crops. It can better protect crops such as corn, sorghum and rice from chloroacetanilides (such as acetochlor) and thiocarbamate herbicides (such as EPTC), especially for sulfonyl Urea and imidazolinone herbicides have better detoxification effect and can reduce the phytotoxicity caused by herbicides. Foreign countries have begun to study its synthesis and application since the 1970s. US Patent U.S.P. 4,038,284 reported a method for synthesizing dichloroacetyl oxazolidine compounds and a method for measuring biological activity. It adds amino alcohol and ketone into benze...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D263/04A01N43/76A01N25/32A01P13/00
Inventor 叶非付颖李颖娇
Owner NORTHEAST AGRICULTURAL UNIVERSITY