Method for preparing N-methyl-2-(2,4-dichlorophenoxy) acetamide

A technology of dichlorophenoxy and chlorophenoxy, applied in the preparation of N-methyl-2-acetamide, in the field of phenoxyamide compounds, can solve the problems of low cost and high product yield

Inactive Publication Date: 2009-03-25
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The technical problem to be solved by the present invention is to use 4-chlorophenol which is less toxic and difficult to hydrolyze as the starting material, and react with halogen ester to obtain the intermediate N-methyl-2-(4-chlorobenzene through ammonolysis. Oxygen) acetamide, obtain target product N-methyl-2-(2,4-dichlorophenoxy) acetamide again through chlorination, this method product yield height, cost is low, has the prospect of suitability for industrialized production

Method used

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  • Method for preparing N-methyl-2-(2,4-dichlorophenoxy) acetamide
  • Method for preparing N-methyl-2-(2,4-dichlorophenoxy) acetamide
  • Method for preparing N-methyl-2-(2,4-dichlorophenoxy) acetamide

Examples

Experimental program
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Effect test

Embodiment 1

[0018] Add 10g (0.05mol) of N-methyl-2-(4-chlorophenoxy)acetamide into a 250mL four-necked flask equipped with a stirrer, thermometer, condenser and dropping funnel, add 60mL of formic acid, and heat to 40°C. A mixture of 9.5g (0.07mol) of sulfuryl chloride and 20mL of formic acid was added dropwise with stirring, and then kept at 40°C for 5h. After the reaction was completed and part of the solvent was removed, the residue was poured into 300 mL of water for water analysis, and after suction filtration, washing and recrystallization, a white solid N-methyl-2-(2,4-dichlorophenoxy)ethane was obtained. Amide 10g, its yield is more than 85%, melting point: 106.5°C-106.8°C. IR(KBr), v / cm -1 : 3317(N-H), 1664(C=O), 1249cm -1 (-O-), 1 HNMR (CDCl 3 ): 7.40 (m, 1H, -C 6 h 5 ), 7.20 (m, 2H, -C 6 h 5 ), 6.60 (q, 1H, -NH-), 4.45 (2H, -CH 2 -), 2.80 (d, 3H, -CH 3 ). Elemental Analysis C 9 h 9 NO 2 Cl 2 , measured value (calculated value) / %: W(C)=46.12(46.18), W(H)=3.84(3.8...

Embodiment 2

[0020] Add 10g (0.05mol) of N-methyl-2-(4-chlorophenoxy)acetamide into a 250mL four-necked flask equipped with a stirrer, thermometer, condenser and dropping funnel, add 60mL of formic acid, and heat to 60°C. A mixture of 9.5g (0.07mol) of sulfuryl chloride and 20mL of formic acid was added dropwise with stirring, and then kept at 60°C for 5h. After the reaction was completed and part of the solvent was removed, the residue was poured into 300 mL of water for water analysis, and after suction filtration, washing and recrystallization, a white solid N-methyl-2-(2,4-dichlorophenoxy)ethane was obtained. Amide 6.5g, the yield is 56%.

Embodiment 3

[0022] Add 10g (0.05mol) of N-methyl-2-(4-chlorophenoxy)acetamide into a 250mL four-necked flask equipped with a stirrer, thermometer, condenser and dropping funnel, add 60mL of formic acid, and heat to 30°C. A mixture of 8.2 g (0.06 mol) of sulfuryl chloride and 20 mL of formic acid was added dropwise with stirring, and then kept at 30° C. for 5 h. After the reaction was completed and part of the solvent was removed, the residue was poured into 300 mL of water for water analysis, and after suction filtration, washing and recrystallization, a white solid N-methyl-2-(2,4-dichlorophenoxy)ethane was obtained. The amide was 5.8 g, and the yield was 49.5%.

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Abstract

The invention discloses a method for preparing N-methyl-2-(2, 4-dichlorophenoxy) acetamide, which comprises the steps: a. 4-chlorophenol, a solvent N, N-dimethylformamide and anhydrous potassium carbonate taken as an acid-binding agent are added into a vessel for reaction; b. 2-(4-chlorophenoxy) methyl acetate and ethanol are added into the vessel for reaction; and c. N-methyl-2-(4-chlorophenoxy) acetamide and the solvent methanoic acid are added into the vessel and dropped with the mixed solution of sulfuric chloride and methanoic acid for reaction, and then the N-methyl-2-(2, 4-dichlorophenoxy) acetamide is obtained after drying. The invention selects initial raw materials with comparatively low toxicity, has high product yield and low cost, and can be used for industrial production.

Description

technical field [0001] The present invention relates to a preparation method of phenoxyamide compounds, more specifically to a phenoxyamide compound containing chlorine on the benzene ring, namely N-methyl-2-(2,4-dichlorophenoxy ) The preparation method of acetamide. Background technique [0002] 2,4-Dichlorophenoxy carboxylic acid compound and its derivatives are systemic and efficient plant growth regulators, which can promote biosynthesis in plants, prevent flower and fruit drop, increase fruit production rate, and increase fruit growth rate , Promote early maturation, and also have a herbicidal effect. When synthesizing 2,4-dichlorophenoxycarboxylic acid compounds and their derivatives, in the past, 2,4-dichlorophenol was mostly used as raw material and halogen carboxylic acid, halogen ester, halogen amide, etc. in alkaline aqueous solution The reaction is obtained, therefore, the raw material halide is easily hydrolyzed; in addition, 2,4-dichlorophenol is more expensi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/20C07C231/12C07C231/02A01P21/00
Inventor 金东元王红高永红陶建伟
Owner SHANGHAI INST OF TECH
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