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Prepn process of safe herbicide prepn of N-dichloroacetyl oxazolidine herbicide

A technology of dichloroacetyl oxazolidine and dichloroacetyl chloride, which is applied in the field of synthesis of herbicide safeners, can solve the problems of high reaction conditions, long reaction time, complicated operation, etc., and achieves mild reaction conditions and short reaction time. Short, high promotional value effect

Inactive Publication Date: 2007-08-22
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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  • Prepn process of safe herbicide prepn of N-dichloroacetyl oxazolidine herbicide

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Experimental program
Comparison scheme
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, which 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 within 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 distilled off under reduced pressure, and the crude product was recrystallized from cyclohexane to obtain compound I with 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, which is equipped with a thermometer, a reflux condenser, and a dropping funnel. Stir at 33-34°C for 1 hour, reflux for about 1.5 hours, cool to -10°C, add 7.5mL of 33% NaOH solution, add dichloroacetyl chloride dropwise, control the rate of addition, and control the temperature of the reaction system at -10-0 After the dropwise addition, the organic phase was washed with water to neutrality, and the organic phase was dried with anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the crude product was separated by silica gel column chromatography, and the solvent was distilled off under reduced pressure to obtain white crystals, compound II, with a yield of 60.4%.

Embodiment approach 3

[0030] Add 0.067mol 2-methyl-2-aminopropanol, 0.067mol cyclopentanone, and 20.0mL chloroform into a three-necked flask, which 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 within 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 distilled off under reduced pressure, and the crude product was separated by silica gel column chromatography, the solvent was distilled off 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 belongs to the field of organic synthesis and pesticide synthesis research, in particular to a method for synthesizing a herbicide safener. Background technique [0002] Dichloroacetyloxazolidines It is a new type of herbicide safener, and it is a good antidote for chloroacetanilide and thiocarbamate herbicides, and can be used as a sulfonylurea and imidazolinone herbicide in grass crop fields Safener, can better protect crops such as corn, sorghum and rice from the damage of chlorinated acetanilides (such as acetochlor) and thiocarbamate herbicides (such as EPTC), especially for sulfonyl Urea and imidazolinone herbicides have better detoxification effects, which can reduce the phytotoxicity caused by herbicides. Foreign countries have begun to study its synthesis and application since the 1970s. U.S. Patent U.S.P. 4,038,284 reported a method for the synthesis of dichloroacetyl oxazolidine compounds and a method for measuring their bio...

Claims

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Application Information

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