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Synthesis method of weedicide mesotrione intermediate 2-nitro-4-mesyltoluene

A technology of mesyltoluene and mesotrione, which is applied in the fields of chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve problems such as unfavorable large-scale industrial production, achieve low cost, high yield, The effect of short synthetic routes

Active Publication Date: 2013-05-29
JIANGSU FLAG CHEM IND
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, it is not conducive to large-scale industrial production

Method used

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  • Synthesis method of weedicide mesotrione intermediate 2-nitro-4-mesyltoluene
  • Synthesis method of weedicide mesotrione intermediate 2-nitro-4-mesyltoluene
  • Synthesis method of weedicide mesotrione intermediate 2-nitro-4-mesyltoluene

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Embodiment 1

[0044] Embodiment 1 intermediate two 2-nitro-4-methanesulfonyl toluene

[0045] (1) Preparation of intermediate - 3-nitro-4-methylbenzenesulfonyl chloride

[0046]Add 130.8 grams of 98% chlorosulfonic acid (1.1 moles) into a 500 ml four-necked bottle equipped with a thermometer, agitator, reflux condenser and tail gas absorption device, heat up and keep it at 110-115 °C, and dissolve 137.8 grams of 99.5% chlorosulfonic acid Slowly drop o-nitrotoluene (1 mole) into the four-necked flask, and the dropwise addition is completed in about 3 hours. Then, the temperature of the reaction mixture is raised to 110-115°C, and the reaction is kept for 3 hours. The hydrogen chloride gas tail gas generated during the reaction is absorbed through the tail gas absorption system. Add 5 grams of N,N-dimethylformamide catalyst, keep 43-53 °C and add 138.2 grams of 99% thionyl chloride (1.15 moles) dropwise within 4-5 hours. After dropping, keep warm and control 60-65 °C After reacting for 3 ho...

Embodiment 2

[0049] Embodiment two, intermediate two 2-nitro-4-methanesulfonyltoluene

[0050] (1) Preparation of intermediate - 3-nitro-4-methylbenzenesulfonyl chloride

[0051] Add 142.5 grams of 98% chlorosulfonic acid (1.20 moles) into a 500 ml four-necked bottle equipped with a thermometer, stirrer, reflux condenser and tail gas absorption device, heat up and keep it at 110-115 ° C, and dissolve 137.8 grams of 99.5% Slowly drop o-nitrotoluene (1.0 mol) into the four-necked flask, and the dropwise addition is completed in about 3 hours. Then, the temperature of the reaction mixture is raised to 110-115°C, and the reaction is kept for 3 hours. The hydrogen chloride gas tail gas generated during the reaction is absorbed through the tail gas absorption system. Add 5 grams of catalyst N,N-dimethylformamide, keep 43-53 °C and add 133.8 grams of 99% thionyl chloride (1.125 moles) dropwise within 4-5 hours. After dropping, keep warm and control the reaction at 60-65 °C After 3 hours, HPLC m...

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Abstract

The invention discloses a synthesis method of weedicide mesotrione intermediate 2-nitro-4-mesyltoluene, which comprises the following steps: carrying out sulfonation reaction on 2-nitrotoluene and chlorosulfonic acid, and continuing adding catalyst and thionyl chloride to carry out acyl-chlorination reaction, thereby preparing 3-nitro-4-methylbenzene sulfonyl chloride; and finally, reacting with sodium sulfite, sodium carbonate and chloroacetic acid to synthesize the 2-nitro-4-mesyltoluene. The synthesis method has the advantages of high yield and favorable product purity, saves the synthesis cost, and implements low-pollution production.

Description

technical field [0001] The invention belongs to the field of chemical industry, and in particular relates to a new synthesis method of an intermediate 2-nitro-4-methylsulfonyltoluene of the herbicide mesotrione. Background technique [0002] 2-nitro-4-methylsulfonyltoluene is an important intermediate in the synthesis of the herbicide mesotrione. Mesotrione (Mesotrione, Mesotrione) is a triketone herbicide developed by Syngenta, Switzerland. Its Chinese common name: Mesotrione, chemical name: 2-(2-nitro- 4-thiamphenicol-benzoyl)cyclohexane-1,3-dione, CAS number: 104206-82-8, other Chinese name: Mistone, other Chinese common name: mesotrione. Its molecular formula: C 14 h 13 NO 7 S, molecular weight: 339.3205, structural formula: [0003] [0004] Mesotrione is a pre-emergence and post-emergence broadleaf herbicide in cornfields. It has systemic properties and can effectively control annual broadleaf weeds and some grass weeds in cornfields. It is not only safe for co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C317/14C07C315/00
Inventor 王凤云张胜王正旭吴耀军
Owner JIANGSU FLAG CHEM IND
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