Application of fluorosulfonyl compound to preparation of FSO2N3

A technology of FSO2N3 and fluorosulfonyl, applied in azide acid/azide/halogen azide, organic chemistry, etc., can solve the problems of low safety and poor preparation yield

Active Publication Date: 2019-12-20
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

[0003] The technical problem to be solved by the present invention is aimed at FSO in the prior art 2 N 3 The technical defects o

Method used

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  • Application of fluorosulfonyl compound to preparation of FSO2N3
  • Application of fluorosulfonyl compound to preparation of FSO2N3
  • Application of fluorosulfonyl compound to preparation of FSO2N3

Examples

Experimental program
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Effect test

Embodiment 1

[0050] Preparation of 1-(fluorosulfonyl)-2,3-dimethyl-1H-imidazole trifluoromethanesulfonate

[0051]

[0052] 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 sulfate, and the filtrate is concentrated by a rotary evaporator (the boiling point of 2-methyl-1H-...

Embodiment 2

[0055] Preparation of 1-(fluorosulfonyl)-3-methyl-1H-imidazole trifluoromethanesulfonate

[0056]

[0057] 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 product 1H-imidazole-1 - a mixed solution of sulfonyl fluoride [compound 6], dichloromethane an...

Embodiment 3

[0060] Preparation of 1-(fluorosulfonyl)-1H-imidazolium bisulfate

[0061]

[0062] 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 140torr), and the product 1H-imidazole-1-sulfonyl fluoride is obtained...

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Abstract

The invention discloses application of fluorosulfonyl compound I to preparation of FSO2N3. According to application of the fluorosulfonyl compound I to preparation of the FSO2N3, the fluorosulfonyl compound I comprises a positive ion and a negative ion, the positive ion is presented as a formula A: please see the specification for the formula, wherein R1, R2, R3 and R4 are individually hydrogen orC1-C6 alkyl group, or the R3 and the R4 and a carbon atom between the R3 and the R4 commonly form unsaturation C5-C8 cyclo-hydrocarbyl. The required FSO2N3 can be safely, simply, conveniently and quickly prepared in high yield by adopting the fluorosulfonyl compound; and the prepared FSO2N3 can be directly used in subsequent reactions without treatment.

Description

technical field [0001] The present invention relates to a kind of fluorosulfonyl compound in the preparation of FSO 2 N 3 in the application. Background technique [0002] In the 1966 patent (US3418088A) of DuPont, the United States reported the use of LiN 3 , 4 times the amount of SO 2 f 2 in me 2 Reaction at room temperature in O / DMF for 19 hours and distillation to obtain FSO 2 N 3 ; The reaction time is long, relatively dangerous and the yield is only 35%. J.K.Ruff reported using NaN in 1965 3 , S 2 o 5 f 2 in MeNO 2 FSO was distilled after 14 hours of reaction 2 N 3 ; The reaction yield is only 65% ​​(Inorg.Chem.1965, 4 (4), 567). Due to the lack of a more efficient and safe preparation method to prepare FSO 2 N 3 , coupled with the danger of its existence, limits the FSO 2 N 3 properties; no reports on its application have been reported so far. Contents of the invention [0003] The technical problem to be solved by the present invention is aimed ...

Claims

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Application Information

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IPC IPC(8): C01B21/08C07D233/58C07D235/22
CPCC01B21/08C07D233/58C07D235/22
Inventor 董佳家巴里.夏普利斯孟根屹郭太杰马天成
Owner 中宏鑫投资控股(深圳)有限公司
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