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A kind of method of benzenesulfonyl chloride compound and secondary amine metal-free catalyzed synthesis of benzenesulfonamide compound

A technology based on benzenesulfonyl chlorides and metal-free catalysis, which is applied in the preparation of sulfonamides and organic chemistry, and achieves broad application prospects, simple recycling, and no pollution in recycling

Active Publication Date: 2022-05-13
HUNAN AGRICULTURAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there are no public documents and patent applications using iodine-containing compounds to catalyze S-N bond coupling in air to form benzenesulfonamide compounds at home and abroad.

Method used

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  • A kind of method of benzenesulfonyl chloride compound and secondary amine metal-free catalyzed synthesis of benzenesulfonamide compound
  • A kind of method of benzenesulfonyl chloride compound and secondary amine metal-free catalyzed synthesis of benzenesulfonamide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Embodiment 1: the synthesis of 1-(benzenesulfonyl) pyrrolidine

[0014] Add substrate 53.0mg (0.3mmol) benzenesulfonyl chloride and 42.7mg (0.6mmol) tetrahydropyrrole, catalyst 4.3mg (0.03mmol) ammonium iodide, 0.12mL tert-butyl hydroperoxide and 2mL THF in air 30mL sealed tube. Then put the sealed tube into an oil bath at 100°C for 10 h. After the reaction, the reaction solution was cooled to room temperature, 40 mL of saturated brine was added, extracted three times with 100 mL of ethyl acetate, and the organic layers were combined. The organic layer was dried with anhydrous sodium sulfate, filtered, and the filtrate was distilled under reduced pressure and separated by silica gel column chromatography (ethyl acetate / petroleum ether: 1 / 2 as eluent) to obtain 101.5 mg of yellow oily liquid, yield 90% .

[0015] The resulting liquid was subjected to hydrogen spectroscopy 1 H NMR (400MHz, CDCl 3 )δ7.83(d, J=8.0Hz, 2H), 7.60(d, J=8.0Hz, 1H), 7.54(t, J=8.0Hz, 2H), 3.2...

Embodiment 2

[0016] Example 2: Synthesis of 1-((4-fluorophenyl)sulfonyl)pyrrolidine

[0017] Substrate 58.4mg (0.3mmol) 4-fluorobenzenesulfonyl chloride and 42.7mg (0.6mmol) tetrahydropyrrole, catalyst 4.3mg (0.03mmol) ammonium iodide, 0.12mL tert-butyl hydroperoxide and 2mL THF, in Add to 30mL sealed tube under air environment. Then put the sealed tube into an oil bath at 120°C for 6 h. After the reaction, the reaction solution was cooled to room temperature, 40 mL of saturated brine was added, extracted three times with 100 mL of ethyl acetate, and the organic layers were combined. The organic layer was dried with anhydrous sodium sulfate, filtered, and the filtrate was distilled under reduced pressure and separated by silica gel column chromatography (ethyl acetate / petroleum ether: 1 / 2 was used as eluent) to obtain 148.4 mg of white solid with a yield of 85%. .

[0018] The resulting solid was subjected to hydrogen spectroscopy 1 H NMR (400MHz, CDCl 3 )δ7.79-7.76 (m, 2H), 7.14 (t, ...

Embodiment 3

[0019] Example 3: Synthesis of 4-(sulfonyl-1-pyrrolidinyl)benzonitrile

[0020] Substrate 32.4mg (0.3mmol) 4-cyanobenzenesulfonyl chloride and 42.7mg (0.6mmol) tetrahydropyrrole, catalyst 11.1mg (0.03mmol) tetrabutylammonium iodide, 0.12mL tert-butyl hydroperoxide and Add 2mLTHF to a 30mL sealed tube under air. Then put the sealed tube into an oil bath at 100°C for 10 h. After the reaction, the reaction solution was cooled to room temperature, 40 mL of saturated brine was added, extracted three times with 100 mL of ethyl acetate, and the organic layers were combined. The organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was distilled under reduced pressure and separated by silica gel column chromatography (ethyl acetate / petroleum ether: 1 / 2 as eluent) to obtain 128.6 mg of white solid with a yield of 91%. .

[0021] The resulting solid was subjected to hydrogen spectroscopy 1 H NMR (400MHz, CDCl 3 ): δ7.93(d, J=8.4Hz, 2H), 7.80(d, J=8.3Hz, ...

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Abstract

A metal-free catalyzed method for synthesizing benzenesulfonyl chloride compounds and secondary amines to benzenesulfonamide compounds, the method is to use benzenesulfonyl chloride compounds and secondary amines as substrates and iodine-containing compounds as catalysts in an air environment , tert-butyl hydroperoxide is an oxidizing agent, and an S-N bond coupling reaction occurs in a solvent to generate benzenesulfonamide compounds. The catalyst used in the method is simple and easy to obtain, stable in the air, easy to recover and non-polluting, and the invention has broad application prospects in medicine synthesis and industrial production.

Description

technical field [0001] The invention belongs to the field of organic synthesis and pharmaceutical synthesis, and relates to a synthesis method of benzenesulfonamide compounds, in particular to a method for synthesizing benzenesulfonyl chloride compounds and secondary amines with iodine-containing compounds under metal-free catalytic conditions. . Background technique [0002] Benzenesulfonamide compounds are often obtained by the amination reaction of benzenesulfonyl chloride. Such substances have potent antifungal, bacterial, anticancer, antipsychotic, anti-HIV protease inhibitors and other biological activities. Most have been used as potent cysteine ​​protease and carbonic protease inhibitors. Therefore, the development of synthetic methods of benzenesulfonamides has important practical value. [0003] At present, there are many synthetic methods for benzenesulfonamide compounds under the catalysis of transition metals, for example: 2 In the catalytic system, through ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D295/26C07C303/36C07C311/29
CPCC07C303/36C07D295/26C07C311/29
Inventor 桂清文蒋红梅覃晓丽李周超腾帆熊志远杨祥
Owner HUNAN AGRICULTURAL UNIV
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