Fluorine-containing sulfonyl compound as well as intermediate, preparation method and application thereof

A compound and sulfonyl technology, applied in the field of fluorine-containing sulfonyl compounds, can solve the problems of high toxicity of fluorosulfonylation reagents, difficulty in preparation, and impossibility of popularization and application

Active Publication Date: 2018-03-30
中宏鑫投资控股(深圳)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to overcome the defects of the current fluorosulfonylation reagents in the field, such as high toxicity, inability to pop

Method used

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  • Fluorine-containing sulfonyl compound as well as intermediate, preparation method and application thereof
  • Fluorine-containing sulfonyl compound as well as intermediate, preparation method and application thereof
  • Fluorine-containing sulfonyl compound as well as intermediate, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] Preparation of 1-(fluorosulfonyl)-2,3-dimethyl-1H-imidazole trifluoromethanesulfonate

[0078]

[0079] Preparation of Scheme 1 1-(fluorosulfonyl)-2,3-dimethyl-1H-imidazole trifluoromethanesulfonate

[0080] Add 2-methylimidazole [Compound 1] (49.3g, 600mmol) to the suspension of sodium carbonate (159.1g, 1500mmol) and acetonitrile (600mL) at room temperature, and the reaction system is pumped to negative pressure with a balloon to introduce sulfuryl fluoride Gas [compound 2] (18L, 730mmol), stirred overnight, TLC (petroleum ether: ethyl acetate = 10:1, product R f=0.44) to detect the completion of the reaction, the reaction solution is filtered with silica gel (10-40 mesh), the filter cake is washed with dichloromethane (600mL), the filtrate is extracted with distilled water (3000mL×3), and the aqueous phase is combined with dichloromethane (600mL ) back extraction, the combined organic phases are washed with saturated brine (600mL), dried over anhydrous sodium sul...

Embodiment 2

[0083] Preparation of 1-(fluorosulfonyl)-3-methyl-1H-imidazole trifluoromethanesulfonate

[0084]

[0085] Preparation of Scheme 2 1-(fluorosulfonyl)-3-methyl-1H-imidazole trifluoromethanesulfonate

[0086] Add imidazole [compound 5] (1.36g, 20mmol) to sodium carbonate (4.2g, 40mmol) acetonitrile (80mL) suspension at room temperature. ] (0.6L, 25mmol), stirred overnight, TLC (petroleum ether: ethyl acetate=10:1, product R f =0.48) to detect the completion of the reaction, add water (200mL) to the system to separate the phases of the reaction solution, extract with dichloromethane (200mL×3), wash the organic phases with saturated brine (150mL) after merging, dry over anhydrous magnesium sulfate, and Filter through algal earth, and concentrate the filtrate to about 40mL by a rotary evaporator (1H-imidazole-1-sulfonyl fluoride has a low boiling point, the temperature during concentration is controlled below 28°C, and the pressure is controlled above 140torr) to obtain the pro...

Embodiment 3

[0089] Preparation of 1-(fluorosulfonyl)-1H-imidazolium bisulfate

[0090]

[0091] Preparation of Scheme 3 1-(fluorosulfonyl)-1H-imidazolium bisulfate

[0092] Add imidazole [compound 5] (0.68 g, 10 mmol) to sodium carbonate (2.1 g, 20 mmol) acetonitrile (40 mL) suspension at room temperature, and then use a balloon to introduce sulfuryl fluoride gas [compound 2 ] (0.4L, 16mmol), stirred overnight, TLC (petroleum ether: ethyl acetate=10:1, product R f =0.48) to detect the completion of the reaction, add water (100mL) to the system to separate the phases of the reaction solution, extract with dichloromethane (80mL×3), wash with saturated brine (60mL) after the organic phases are combined, dry over anhydrous magnesium sulfate, and Filter through algal earth, and concentrate the filtrate to 20mL by a rotary evaporator (1H-imidazole-1-sulfonyl fluoride has a low boiling point, the temperature during concentration is controlled below 28°C, and the pressure is controlled above ...

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PUM

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Abstract

The invention discloses a fluorine-containing sulfonyl compound as well as an intermediate, a preparation method and application thereof. The fluorine-containing sulfonyl compound disclosed by the invention comprises positive ions and negative ions, wherein the positive ions are shown as the formula I. The fluorine-containing sulfonyl compound can react with substrates to effectively synthetize the fluorine-containing sulfonyl compound; the toxicity is low; the preparation is simple; the use is convenient; the fluorine-containing sulfonyl compound is in a solid stable state at normal temperature. In addition, the substrate applicability of the compound is extremely wide, and a phenol compound and an amine compound can be included; the fluorine-containing sulfonyl compound is a unique solidformation reagent capable of realizing the chemical conversion at present, so that important academic and application values are realized. The formula I is shown in the description.

Description

technical field [0001] The invention relates to a fluorine-containing sulfonyl compound, its intermediate, preparation method and application. Background technique [0002] The high-valent fluorides of the main group have high chemical stability, but their activation under specific conditions can realize the conversion and linkage of extremely efficient chemical bonds. This unique combination of stability and reactivity determines that this type of compound will have unique potential applications in organic synthetic chemistry, material chemistry, chemical biology and medicinal chemistry. The success of the hexavalent sulfur-fluorine exchange reaction Sulfur (VI) Fluoride Exchange (SuFEx) is due to the special reactivity of the hexavalent sulfur-fluorine bond. Since Professor K.Barry Sharpless and Jiajia Dong first proposed and successfully realized the hexavalent sulfur-fluorine exchange reaction in 2014 (Angew.Chem.Int.Ed.2014, 9430), this type of reaction has been used i...

Claims

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Application Information

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IPC IPC(8): C07D233/56C07D235/08C07C309/06C07C303/32C07C305/26C07C317/22C07J31/00C07D513/04C07D291/08C07D491/22C07C323/20C07D311/16C07D311/14C07D215/32C07D213/65C07D327/10C07C307/00C07C317/48C07D295/26C07D207/48C07D211/96C07D205/04C07D267/18
CPCC07B2200/07C07C305/26C07C307/00C07C317/22C07C317/48C07C323/20C07D205/04C07D207/48C07D211/96C07D213/65C07D215/32C07D233/56C07D235/08C07D267/18C07D291/08C07D295/26C07D311/14C07D311/16C07D327/10C07D491/22C07D513/04C07J31/006
Inventor 董佳家杨倩郭太杰詹雄杰孟根屹
Owner 中宏鑫投资控股(深圳)有限公司
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