Method for synthesizing herbicide pretilachlor by one-pot method

A technology of pretilachlor and herbicide, applied in the field of synthetic herbicide pretilachlor, can solve the problems of long process flow, difficult control of monoalkylation, high production cost, etc., achieve short process flow, reduce production cost, and use raw materials high rate effect

Inactive Publication Date: 2011-09-07
NANTONG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The first method is rarely used in industry due to the high price of brominated hydrocarbons; the second method, due to the problem of catalysts, still has problems in large-scale industrial use; the first and third methods still exist Mono-alkylation ...

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Add 149 grams (1.0 mol) of 2,6-diethylaniline and 100 ml of toluene into a 2000ml three-necked flask equipped with a stirrer, a thermometer and an air condenser, and add 24 grams (1.0 mol) of sodium hydride ( 40 grams of 60% industrial grade sodium hydride containing mineral oil (obtained by washing with toluene), control the addition speed, after the bubbles basically disappear, add 122.5 grams (1.0 mole) of chloroethyl propyl ether dropwise, after the addition, 80 ° C React for 1 hour, then add 113 grams (1.0 moles) of chloroacetyl chloride dropwise, continue to react at 80°C for 4 hours after the addition, after cooling to room temperature, add 200 ml of water, stir for 5 minutes, let stand, separate layers, organic The phase was washed twice with saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure (recovery) to obtain 234 g of pretilachlor with a yield of 75% and a content of 90.6%.

Embodiment 2

[0016] Add 149 grams (1.0 mol) of 2,6-diethylaniline and 100 ml of toluene into a 2000ml three-necked flask equipped with a stirrer, a thermometer and an air condenser, and add 24 grams (1.0 mol) of sodium hydride ( 40 grams of 60% industrial-grade sodium hydride containing mineral oil (obtained by washing with toluene), control the addition speed, and after the bubbles basically disappear, add 122.5 grams (1.0 moles) of chloroethyl propyl ether dropwise, after the addition, 100 ° C React for 2 hours, then add 113 grams (1.0 moles) of chloroacetyl chloride dropwise, continue to react at 90°C for 4 hours after the addition, after cooling to room temperature, add 200 ml of water, stir for 5 minutes, let stand, separate layers, organic The phase was washed twice with saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure (recovery) to obtain 243 g of pretilachlor with a yield of 78% and a content of 91.3%.

Embodiment 3

[0018] Add 149 grams (1.0 mol) of 2,6-diethylaniline and 100 ml of toluene into a 2000ml three-necked flask equipped with a stirrer, a thermometer and an air condenser, and add 24 grams (1.0 mol) of sodium hydride ( 40 grams of 60% mineral oil-containing industrial grade sodium hydride, obtained by washing with toluene), control the addition speed, and after the bubbles basically disappear, add 122.5 grams (1.0 mole) of chloroethyl propyl ether dropwise, after the addition, react at 120 ° C After 2 hours, 113 grams (1.0 mole) of chloroacetyl chloride was added dropwise. After the addition, the reaction was continued at 100°C for 4 hours. After cooling to room temperature, 200 ml of water was added and stirred for 5 minutes. Wash twice with saturated brine, dry over anhydrous sodium sulfate, and distill off the solvent under reduced pressure (recovery) to obtain 256 g of pretilachlor with a yield of 82% and a content of 93.5%.

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Abstract

The invention discloses a method for synthesizing herbicide pretilachlor by a one-pot method, which comprises the following steps of: reacting 2,6-diethylaminobenzene with strong base in a nonprotonic solvent to generate amino sodium salt; then reacting the amino sodium salt with chloroethyl propyl ether to generate pretilachlor intermediate 2,6-diethyl-N-(2-propoxyethyl) phenylamine; and leadingthe intermediate 2,6-diethyl-N-(2-propoxyethyl)phenylamine not subjected to separation and chloroacetic chloride to carry out acylation reaction in the same reactor to obtain pretilachlor. The invention has the advantages of high reaction selectivity, high yield, short process flow, high utilization ratio of raw materials, reduced production cost and higher productive and practical value.

Description

technical field [0001] The invention relates to a method for synthesizing the herbicide pretilachlor. Background technique [0002] Pretilachlor belongs to 2-chlorinated acetanilide herbicides. It is a high-efficiency, low-toxicity herbicide specially used for paddy fields at bud stage. , cattle felt and other weeds are widely used and highly appraised by the agricultural plant protection department. At present, the most common synthetic method of pretilachlor is to use 2,6-diethylaniline as the starting material, through the monoalkylation reaction of amino group, to obtain 2,6-diethyl-N-(2-propoxy Ethyl) aniline, and then acylated with chloroacetyl chloride. The key is the first step of monoalkylation reaction. If 2,6-diethylaniline reacts with chloroethyl propyl ether and other substances, dialkylation is difficult to avoid. In order to avoid dialkylation, 2, The way of excessive 6-diethylaniline brings the problem of excessive raw material in the product, so these two...

Claims

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Application Information

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IPC IPC(8): C07C233/18C07C231/02A01N37/26A01P13/00
Inventor 吴锦明沈爱宝明亮施磊张海军
Owner NANTONG UNIVERSITY
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