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Preparation method of 1-(2,2-difluoroethoxy)-6-trifluoromethyl-N-([1,2,4]triazolezol[1,5-C] pyrimidine-2-)benzsulfamide

A technology of difluoroethoxy and trifluoromethyl, which is applied in the field of preparation of 1--6-trifluoromethyl-N-benzenesulfonamide, can solve the problems of low marketability and high price, and achieve Improvement of reaction time and yield, reduction of production cost, and simplification of reaction conditions

Inactive Publication Date: 2011-04-20
孙智华 +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] 1-(2,2-difluoroethoxy)-6-trifluoromethyl-N-([1,2,4]triazol[1,5-c]pyrimidine-2-)benzenesulfonamide is Disclosed by U.S. Tao Nongke Company (Dow Agro-Sciences) in 1999 U.S. Patent (US5858924), the 1-(2,2-difluoroethoxy)-6-trifluoromethyl involved in this patent -N-([1,2,4]triazol[1,5-C]pyrimidine-2-)benzenesulfonamide is obtained through 6-trifluoromethyl-2-fluoro Aniline is used as raw material to prepare 6-trifluoromethyl-2-fluorobenzenesulfonyl chloride; in another two patents (US20050215570 and US20020037811) of Dow Company, it is mentioned that methoxymethylene chloride is used as a phenolic hydroxyl protecting group Synthetic method, but the introduction of difluoroethoxy requires the use of expensive and unmarketable 2,2-difluorobromoethane as a reagent

Method used

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  • Preparation method of 1-(2,2-difluoroethoxy)-6-trifluoromethyl-N-([1,2,4]triazolezol[1,5-C] pyrimidine-2-)benzsulfamide

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Embodiment 1

[0054] 1 Synthesis of compound VI

[0055]

[0056] Take a 500ml three-neck reactor, put it into a stirring bar, add 40g m-trifluoromethylphenol, add 210ml dichloromethane, add 100ml N,N-diisopropylethylamine, and stir. Under an ice bath, take 46ml of chloromethoxymethyl ether and slowly add it dropwise with a constant pressure dropping funnel. When dripping, the color changes from green to yellow, and finally to orange-purple, and fog occurs. After dripping, at regular intervals, use a UV lamp, use a silica gel plate to track the reaction, and find that the reaction is slow, and stir overnight at room temperature. Afterwards, dichloromethane was evaporated under reduced pressure, and then distilled under reduced pressure with an oil pump to collect a stable fraction at 68°C. 36.7 g of the product was obtained with a yield of 72%. 1 H-NMR (400MHz, CDCl 3 )δ: 7.42(m, 1H), 7.31-7.23(m, 3H), 5.23(s, 2H), 3.51(s, 3H). 13 C-NMR (100MHz, CDCl 3 )δ: 157.5, 132.1, 129.9, 123....

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Abstract

The invention provides a preparation method of 1-(2,2-difluoroethoxy)-6-trifluoromethyl-N-([1,2,4]triazolezol[1,5-C]pyrimidine-2-)benzsulfamide, comprising the following steps: using a compound represented by formula (IV) as an initial raw material to synthesize a compound represented by formula (III); synthesizing the compound represented by formula (II); finally synthesizing a target compound represented by formula (I). In the invention, two phenolic alcohols are jointed to form ether, thereby preventing from using costly non-marketization 2,2-difluorobromoethane for introducing difluoroethoxy as a reagent; in the process of synthesizing target product, besides 3,5-dimethyl pyridine and dimethyl sulfoxide, a catalytic amount of 18-crown-6 crown ether is used to improve the reaction timeand reaction yield. The invention simplifies the reaction conditions, optimizes the synthesis process, enhances the reaction yield, and reduces production cost, thereby greatly improving the synthesis effect. The reaction formula is represented as follows.

Description

technical field [0001] The present invention relates to 1-(2,2-difluoroethoxy)-6-trifluoromethyl-N-([1,2,4]triazol[1,5-C]pyrimidine-2-)benzene Preparation method of sulfonamide. Background technique [0002] 1-(2,2-difluoroethoxy)-6-trifluoromethyl-N-([1,2,4]triazol[1,5-C]pyrimidine-2-)benzenesulfonamide ( penoxsulam), its chemical structure is as follows: [0003] [0004] 1-(2,2-difluoroethoxy)-6-trifluoromethyl-N-([1,2,4]triazol[1,5-c]pyrimidine-2-)benzenesulfonamide is A post-emergence herbicide developed by Dow Agro-Sciences in the United States, it is a triazolopyrimidine sulfonamide herbicide, which works by inhibiting acetolactate synthase (ALS). [0005] As a broad-spectrum deleathering agent for paddy fields, it can effectively control barnyardgrass (including barnyardgrass resistant to propanil, quinclorac and anti-acetyl-CoA carboxylase), stephenia and annual Cyperaceae weeds, It is also effective against many broad-leaved weeds, such as Heteranthera limos...

Claims

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Application Information

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IPC IPC(8): C07D487/04C07C323/20C07C319/20
Inventor 孙智华徐菁利王晗李亚温坤范尔康
Owner 孙智华
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