Mesosulfuron-methyl synthetic method

The technology of methyldisulfuron-methyl and the methyldisulfuron-methyl is applied in the field of preparation of organic compounds, can solve the problems of complicated synthesis steps, high production cost, poor practicability, etc. Practical effect

Active Publication Date: 2013-10-02
JIANGSU REPONT PESTICIDE FACTORY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] U.S. Patent US6538150 discloses using p-toluonitrile as a raw material to realize the synthesis of methylsulfuron-methyl through eight steps of nitration, oxidation, esterification, reduction, mesylation, diazotization-sulfonation, ammonolysis and condensation , although the raw materials in this route are cheap and easy to obtain, the synthesis steps are cumbersome, the yield is low (12.4%), the reduction reaction requires high pressure (1700kPa), and high-risk reagents such as toxic gas sulfur dioxide are used
[0011] To sum up, in the prior art, the synthesis methods of methylsulfuron-methyl have their own disadvantages, such as unavailable raw materials, cumbersome and complicated operations, often using high-risk reagents such as sodium azide or toxic gas sulfur dioxide, and the reduction reaction also requires high pressure. (1700kPa), resulting in high production costs, low yield (12.4%), and poor practicability

Method used

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  • Mesosulfuron-methyl synthetic method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] The synthetic method of methylsulfuron-methyl, the steps are as follows:

[0049] 1) Preparation of 2-methyl-5-aminocarbonylbenzenesulfonamide (2)

[0050] Add 13.6g p-toluic acid (0.1mol), 60.0mL 1,2-dichloroethane and 14.5mL thionyl chloride (0.2mol) into the reaction flask, stir to dissolve, add 25.3mL chlorosulfonic acid (0.4 mol), after the addition, the temperature was raised to 60°C. After reacting for 5 hours, the solvent, thionyl chloride and chlorosulfonic acid were distilled off under reduced pressure, and the residue was cooled and added dropwise to 100mL of ammonia water, the solid precipitated, filtered, washed with water until neutral, and dried to obtain (2) 18.2g, yield: 85.2%.

[0051] 2) Preparation of 5-aminocarbonyl saccharin (3)

[0052] Add 21.4g (2) (0.1mol) and 40mL98% concentrated sulfuric acid into the reactor, stir and cool to 0~5°C, add 88.4g potassium dichromate (0.3mol) and 60mL98% concentrated sulfuric acid dropwise within 0.5h of the...

Embodiment 2

[0064] The synthetic method of methylsulfuron-methyl, the steps are as follows:

[0065] 1) Preparation of 2-methyl-5-aminocarbonylbenzenesulfonamide (2)

[0066] Add 13.6g p-toluic acid (0.1mol), 50.0mL 1,2-dichloroethane and 21.7mL thionyl chloride (0.3mol) into the reaction flask, stir to dissolve, add 19.0mL chlorosulfonic acid (0.3 mol), after the addition, the temperature was raised to 60°C. After reacting for 5 hours, the solvent, thionyl chloride and chlorosulfonic acid were distilled off under reduced pressure, and the residue was cooled and added dropwise to ammonia water (ice bath). The solid precipitated, filtered, washed with water until neutral, and dried to obtain (2) 17.6g. Yield: 82.2%.

[0067] 2) Preparation of 5-aminocarbonyl saccharin (3)

[0068] Add 21.4g (2) (0.1mol) and 40mL98% concentrated sulfuric acid into the reactor, stir and cool to 0~5°C, add 89.4g sodium dichromate (0.3mol) and 50mL98% concentrated sulfuric acid dropwise within 0.5h The mix...

Embodiment 3

[0080] The synthetic method of methylsulfuron-methyl, the steps are as follows:

[0081] a. Add the raw materials p-toluic acid, organic solvent I and thionyl chloride into the reactor, stir to dissolve, add chlorosulfonic acid at room temperature, react at 30°C for 6 hours, and distill off the unreacted raw materials under reduced pressure , the raffinate was cooled to room temperature, added dropwise to ammonia water, the solid was precipitated, filtered, washed with water to pH 7-8, and dried to obtain 2-methyl-5-aminocarbonylbenzenesulfonamide;

[0082] The molar ratio of p-toluic acid: chlorosulfonic acid: thionyl chloride: organic solvent I is 1:3:2:5;

[0083] The ammonia water is NH 3 The mass percentage content is 25% ammoniacal liquor, and the mass ratio of described raffinate and ammoniacal liquor is 1:10;

[0084]b. Add 2-methyl-5-aminocarbonylbenzenesulfonamide and concentrated sulfuric acid into the reactor, stir and cool to 0-10°C, add oxidant and concentrated...

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Abstract

The invention discloses a mesosulfuron-methyl synthetic method. The mesosulfuron-methyl synthetic method is characterized in that mesosulfuron-methyl is prepared from raw materials such as paratoluic acid by adopting the seven steps of chlorosulfonation-ammonolysis, oxidation, dehydration, reduction, alcoholysis, methyl sulfone chloride acylation and condensation. The mesosulfuron-methyl synthetic method provided by the invention has the advantages of being low in cost of the raw materials, easy in availability of the raw materials, simple in operation and mild in conditions, having low requirements on equipment, high yield and strong practicability and being suitable for industrial production.

Description

technical field [0001] The invention belongs to the preparation of organic compounds, and relates to a synthesis method of methylsulfuron-methyl. The mesosulfuron-methyl prepared by the invention is especially suitable for pesticide herbicides. Background technique [0002] Mesosulfuron-methyl, also known as Mesosulfuron-methyl, chemical name 2-[(4,6-dimethoxypyrimidine-2-aminocarbonyl)aminosulfonyl]-α-(methylsulfuronyl) Amino) methyl p-toluate is a novel sulfonylurea herbicide developed by Bayer Corporation of Germany in 2002, which can effectively inhibit the synthesis of acetolactate synthase, and the weed leaves stop growing and gradually wither after absorbing the drug. It has a short residual effect in the soil and does not affect the growth of the following crops. It can be widely used in the weeding of cereal crops and other crop fields. Because of its high efficiency, low toxicity, and environmental friendliness, its synthesis has received extensive attention at h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/52
Inventor 李鸿波马昌鹏韩邦友钱圣利李梅芳开永茂
Owner JIANGSU REPONT PESTICIDE FACTORY
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