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Mesosulfuron preparation method

The technology of methyldisulfuron-methyl and the methyldisulfuron-methyl is applied in the field of preparation of methyldisulfuron-methyl, which can solve the problems of low yield and the like, and achieve the effects of improved yield, easy availability of raw materials and convenient operation.

Active Publication Date: 2019-06-18
YANGZHOU UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this route, the requirements for diazotization reaction conditions are relatively high, and the yield is low, and only this route can be put into industrial production at present, so it is necessary to develop a new synthetic route with simple operation and high yield

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Preparation of 4-bromo-3-nitrobenzaldehyde (compound 2)

[0064] First add 550mg of sodium nitrate and 6mL of sulfuric acid into a 25mL round-bottomed flask, stir until transparent at room temperature, then slowly add 1g of p-bromobenzaldehyde, and react at room temperature for 1 hour after the addition. After the reaction is over, pour the reaction mixture into Ice water, and then filtered with suction to obtain a milky white solid as compound 2, with a yield of 94%.

[0065] The product data is: 1 H NMR (400 MHz, Chloroform-d) δ 10.03 (d, J=2.0 Hz, 1H), 8.30 (d, J=2.2 Hz, 1H), 7.94 (q, J=2.0 Hz, 2H).

Embodiment 2

[0067] Preparation of 4-cyano-3-nitrobenzaldehyde (compound 3)

[0068] 1) Add 1g of 4-bromo-3-nitrobenzaldehyde, 429mg of cuprous cyanide and 10mL of DMF into a 50mL round bottom flask, react at 140°C for 1 hour, stop the reaction, filter with suction, and take the filtrate with ethyl acetate After ester extraction, the organic layer was distilled under reduced pressure, and purified by column chromatography to obtain compound 3 with a yield of 71%.

[0069] 2) Add 1g of 4-bromo-3-nitrobenzaldehyde, 585mg of cuprous cyanide and 10mL of DMF into a 50mL round bottom flask, react at 160°C for 1 hour, stop the reaction, filter with suction, and take the filtrate with ethyl acetate After ester extraction, the organic layer was distilled under reduced pressure, and purified by column chromatography to obtain compound 3 with a yield of 76.4%.

[0070] 3) Add 1g of 4-bromo-3-nitrobenzaldehyde, 585mg of cuprous cyanide and 10mL of DMF into a 50mL round bottom flask, react at 140°C fo...

Embodiment 3

[0074] Preparation of 2-(benzylthio)-4-formylbenzonitrile (compound 4)

[0075] 1) Add 1 g of 4-cyano-3-nitrobenzaldehyde, 739 mg of benzyl mercaptan and 15 mL of DMF into a 50 mL round bottom flask, and cool to 0°C. Dissolve 382mg potassium hydroxide in 1.6ml H 2 An aqueous potassium hydroxide solution was prepared in O, and the potassium hydroxide solution was slowly added dropwise to the above solution under ice-cooling. After the dropwise addition was completed, the mixture was reacted at room temperature for 0.5 hours, and the mixture after the reaction was poured into ice water, and then filtered with suction to obtain a yellow solid as compound 2, which was further purified with a yield of 64.2%.

[0076] 2) Add 1 g of 4-cyano-3-nitrobenzaldehyde, 739 mg of benzyl mercaptan and 15 mL of DMF into a 50 mL round bottom flask, and cool to 0°C. Dissolve 421mg potassium hydroxide in 1.8ml H 2 An aqueous potassium hydroxide solution was prepared in O, and the potassium hydr...

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Abstract

The invention relates to a mesosulfuron preparation method which includes the steps: taking p-bromo benzaldehyde as a starting material, and performing nitration reaction; performing reaction of a reactant and cuprous cyanide, and substituting bromine with cyan; performing nucleophilic substitution reaction on the reactant and benzyl mercaptane, performing reaction on the reactant and hydroxylamine hydrochloride to obtain an oxime intermediate, and reducing oxime by zinc powder; acylating methyl sulfone chloride, hydrolyzing the cyan by concentrated alkaline to obtain carboxylic acid, esterifying the carboxylic acid, chloridizing the esterified carboxylic acid by chlorine, and ammonifying chloridized carboxylic acid by ammonia to obtain 2-methoxycarbonyl-5-methanesulfonyl aminomethyl benzene sulfonamide serving as an intermediate; performing coupling to obtain mesosulfuron serving as a target product. The preparation method is simple to operate, environmentally friendly and high in yield and serves as a novel good mesosulfuron synthesis method.

Description

technical field [0001] The invention relates to the synthesis of organic compounds, in particular to a preparation method of methylsulfuron-methyl. Background technique [0002] Methsulfuron-methyl, also known as Methsulfuron-methyl, chemical name 2-[(4,6-dimethoxypyrimidine 2-aminocarbonyl) aminosulfonyl]-a-(methylsulfonylamino) p-toluic acid Methyl ester belongs to sulfonylurea herbicides. It was discovered for the first time by Horst in 1996. It was mainly developed and sold by German Bayer company in 2002. It mainly stops the growth of weeds by inhibiting acetolactate synthase and achieves weed control. effect. [0003] Methylsulfuron is mainly composed of 4,6-dimethoxy-2-(phenoxycarbonyl)aminopyrimidine and 4-(methylsulfonylaminomethyl)2-sulfonylaminobenzoic acid methyl ester The coupling synthesis of intermediates, in which the former intermediate is easy to obtain, the key lies in the synthesis of the latter intermediate. [0004] At present, the route that can be ...

Claims

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Application Information

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IPC IPC(8): C07D239/52
Inventor 袁宇顾祁昕吕良忠吴磊周鹏
Owner YANGZHOU UNIV
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