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A kind of fluorosulfonyl compound is preparing fso 2 n 3 applications in

A technology of FSO2N3, fluorosulfonyl, applied in the direction of azide acid/azide/halide azide, organic chemistry, etc., can solve the problems of low safety, poor preparation yield, etc., and achieves safe and simple method, high yield high effect

Active Publication Date: 2022-07-19
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 of poor preparation yield and low safety; and a fluorosulfonyl compound is provided in the preparation of FSO 2 N 3 application in

Method used

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  • A kind of fluorosulfonyl compound is preparing fso <sub>2</sub> n <sub>3</sub> applications in
  • A kind of fluorosulfonyl compound is preparing fso <sub>2</sub> n <sub>3</sub> applications in
  • A kind of fluorosulfonyl compound is preparing fso <sub>2</sub> n <sub>3</sub> applications in

Examples

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Effect test

Embodiment 1

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

[0051]

[0052] 2-methylimidazole [compound 1] (49.3g, 600mmol) was added to the suspension of sodium carbonate (159.1g, 1500mmol) in acetonitrile (600mL) at room temperature, and the reaction system was pumped to a negative pressure by a water pump and introduced into sulfuryl fluoride with a balloon Gas [compound 2] (18 L, 730 mmol), stirred overnight, TLC (petroleum ether:ethyl acetate=10:1, product R f = 0.44) detected the completion of the reaction, the reaction solution was filtered with silica gel (10-40 mesh), the filter cake was washed with dichloromethane (600 mL), the filtrate was extracted with distilled water (3000 mL×3), and the aqueous phases were combined with dichloromethane (600 mL). ) back extraction, the organic phases were combined and washed with saturated brine (600 mL), dried over anhydrous sodium sulfate, the filtrate was concentrated by rotary eva...

Embodiment 2

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

[0056]

[0057] To the sodium carbonate (4.2 g, 40 mmol) acetonitrile (80 mL) suspension was added imidazole [compound 5] (1.36 g, 20 mmol) at room temperature, the reaction system was pumped to a negative pressure by a water pump, and then the sulfuryl fluoride gas [compound 2] was introduced with a balloon. ] (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 (200 mL) to the system to separate the reaction liquid, extract with dichloromethane (200 mL × 3), combine the organic phases and wash with saturated brine (150 mL), dry over anhydrous magnesium sulfate, and dry over anhydrous magnesium sulfate. The algae is filtered, and the filtrate is concentrated to about 40mL through a rotary evaporator (the boiling point of 1H-imidazole-1-sulfonyl fluoride is lower, and the temperature...

Embodiment 3

[0060] Preparation of 1-(Fluorosulfonyl)-1H-imidazole hydrogen sulfate

[0061]

[0062] To the sodium carbonate (2.1 g, 20 mmol) acetonitrile (40 mL) suspension was added imidazole [compound 5] (0.68 g, 10 mmol) at room temperature, the reaction system was pumped to negative pressure by a water pump, and then the sulfuryl fluoride gas [compound 2] was introduced with a balloon. ] (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 (100 mL) to the system to separate the reaction liquid, extract with dichloromethane (80 mL × 3), combine the organic phases and wash with saturated brine (60 mL), dry over anhydrous magnesium sulfate, and dry over anhydrous magnesium sulfate. The algae was filtered, and the filtrate was concentrated to 20mL through a rotary evaporator (the boiling point of 1H-imidazole-1-sulfonyl fluoride was lower, the temperature was controlled below 28°C du...

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Abstract

The invention discloses a kind of fluorosulfonyl compound I in the preparation of FSO 2 N 3 applications in . Described fluorosulfonyl compound I is in the preparation of FSO 2 N 3 In the application, wherein, the fluorosulfonyl compound I includes a cation and an anion, and the cation is shown in formula A: wherein, R 1 , R 2 , R 3 and R 4 each independently hydrogen or C 1 ‑C 6 Alkyl, or R 3 and R 4 and the carbon atoms in between to form unsaturated C 5 ‑C 8 Cyclohydrocarbyl. By using the fluorosulfonyl compound of the present invention, the required FSO can be prepared safely, simply, rapidly and in high yield 2 N 3 ; and the resulting FSO 2 N 3 It can be used directly 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 applications in . Background technique [0002] DuPont of the United States reported in the patent (US3418088A) in 1966 that the use of LiN 3 , 4 times the amount of SO 2 F 2 in Me 2 Reaction in O / DMF at room temperature for 19 hours and distillation to obtain FSO 2 N 3 ; the reaction time is long, dangerous and the yield is only 35%. J.K.Ruff reported in 1965 that the use of NaN 3 , S 2 O 5 F 2 in MeNO 2 After 14 hours of reaction, FSO was obtained by distillation 2 N 3 ; the reaction yield is also only 65% ​​(Inorg. Chem. 1965, 4(4), 567). Due to the lack of more efficient and safe preparation methods to prepare FSO 2 N 3 , coupled with the dangers of its existence, limit the 2 N 3 properties; no reports of its application yet. SUMMARY OF THE INVENTION [0003] The technical problem to be solved by the present invention is aimed at...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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