Preparation method of mesosulfuron-methyl

The technology of methyldisulfuron-methyl and the methyldisulfuron-methyl-methyl is applied in the field of preparation of methyldisulfuron-methyl, and can solve the problems such as the inability to realize cyclic application of the catalyst, the environmental pollution of potassium dichromate, the easy corrosion of production equipment, and the like, To achieve the effect of reducing the generation of high COD wastewater, cheap price, and reducing production costs

Active Publication Date: 2019-06-14
YANGZHOU UNIV +1
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  • Application Information

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Problems solved by technology

The patent DE4335297 uses 5-methyl-2-methoxycarbonylbenzenesulfonyl chloride as the starting material, first undergoes amidation reaction, then NBS bromination, azidation, Pd/C catalytic hydrogenation, and then mesylation to obtain Normalize tert-butyl-2-methoxycarbonyl-5-methanesulfonamide methylbenzenesulfonamide, and finally demethylate under the condition of trifluoroformic acid to obtain the target intermediate. Trifluoroformic acid has strong acidity and is easy to corrode production equipment , and the raw materials of this route are not easy to obtain, and the operation is relatively complicated at the same time. The use of sodium azide in industrial production increases the risk of the experiment, which is not conducive to industrial production
[0005] (2) In order to find a relatively convenient synthetic method, Ma Changpeng et al. improved their synthetic route. The patent CN103755603A uses p-toluonitrile as a starti

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  • Preparation method of mesosulfuron-methyl
  • Preparation method of mesosulfuron-methyl
  • Preparation method of mesosulfuron-methyl

Examples

Experimental program
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Effect test

Embodiment 1

[0043] 1) Preparation of methyl 2-(benzylthio)-4-cyanobenzoate (compound 2)

[0044] 1 g of methyl 4-cyano-2-nitrobenzoate, 700 mg of benzyl mercaptan and 10 ml of DMF were added to a 50 mL flask, and the resulting solution was hydrated and cooled to 0°C. Dissolve 520mg potassium hydroxide in 2.2ml 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 at room temperature for 30 minutes, the reaction was completed, and the reaction mixture was poured into ice water, and then filtered with suction to obtain a yellow solid compound 2 with a yield of 80.1%.

[0045] The product data is: 1 H NMR (400MHz, Chloroform-d) δ8.01 (d, J = 8.0Hz, 1H), 7.57 (d, J = 1.5Hz, 1H), 7.40 (dt, J = 7.9, 1.4Hz, 3H), 7.38 –7.23(m,3H),4.15(s,2H),3.91(s,3H).

[0046] 2) Preparation of methyl 4-(aminomethyl)-2-(benzylthio)benzoate (compound 3)

...

Embodiment 2

[0059] 1) Preparation of methyl 2-(benzylthio)-4-cyanobenzoate (compound 2)

[0060] 5 g of methyl 4-cyano-2-nitrobenzoate, 3.5 g of benzyl mercaptan and 45 ml of DMF were added to a 250 mL flask, and the resulting solution was hydrated and cooled to 0°C. Dissolve 2.6g potassium hydroxide in 11ml 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, react at room temperature for 30 minutes, and the reaction is completed. The mixture after the reaction is poured into ice water, and then filtered with suction to obtain a yellow solid as compound 2, with a yield of more than 80%.

[0061] The product data is: 1 H NMR (400MHz, Chloroform-d) δ8.01 (d, J = 8.0Hz, 1H), 7.57 (d, J = 1.5Hz, 1H), 7.40 (dt, J = 7.9, 1.4Hz, 3H), 7.38 –7.23(m,3H),4.15(s,2H),3.91(s,3H).

[0062] 2) Preparation of methyl 4-(aminomethyl)-2-(benzylthio)benzoate (comp...

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Abstract

The invention relates to a preparation method of mesosulfuron-methyl. The method comprises the following steps: taking 4-cyano-2-nitrobenzoate as a starting raw material; firstly performing a nucleophilic substitution reaction with benzyl mercaptan; then, performing reduction hydrogenation by using raney nickel, performing methylsulfonyl acidylation by using methylsulfonyl chloride; then, performing chlorination by using chlorine gas and performing ammoniation by using ammonia gas to obtain a key intermediate, namely 2-methoxycarbonyl-5-methanesulfonyl ammonia toluenesulfonamide; and finally,performing condensation to obtain a target product, namely the mesosulfuron-methyl. A route of the method is mild in reaction process condition; the operation is easy; the method is suitable for industrial mass production; less environmental pollution is caused; and the method is a relatively good novel method for synthesizing the mesosulfuron-methyl.

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 is a new type of sulfonylurea herbicide developed by Bayer AG in 2002. Regarding sulfonylurea herbicides, it is the largest class of herbicides in the world. It mainly works by inhibiting acetolactate synthase , Weed roots and leaves absorb, and conduct in the plant body, thereby prompting weeds to stop growing to achieve the effect of weeding. The herbicide has a good control effect on some broad-leaved weeds such as winter wheat, spring wheat annual grass weeds and chickweed, and the demand for herbicide market in my country is showing an upward trend. [0003] At present, the common synthetic method on the methylsulfu...

Claims

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Application Information

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IPC IPC(8): C07D239/52
Inventor 袁宇于国权吕良忠顾祁昕丁华平吴磊
Owner YANGZHOU UNIV
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