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A kind of preparation method of sulfonamide compound

A technology for sulfonamides and compounds, applied in the field of preparation of sulfonamide compounds, can solve problems such as dependence, and achieve the effects of easy synthesis, good guiding significance and application prospects, and efficient synthesis

Active Publication Date: 2022-04-29
TAIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The existing synthetic methods of sulfonamide compounds still have certain limitations, and to a large extent still rely on sulfonate and sulfonyl chloride compounds

Method used

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  • A kind of preparation method of sulfonamide compound
  • A kind of preparation method of sulfonamide compound
  • A kind of preparation method of sulfonamide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027]

[0028] At room temperature, add 0.2 mmol of nitrosobenzene, 0.3 mmol of sulfur dioxide solid complex DABCO·(SO 2 ) 2 , 0.4mmol p-fluorophenyltetrafluoroborate diazonium salt, plug the reaction tube with a stopper and place it in high-purity argon to replace the gas, so that the system is in anhydrous and oxygen-free conditions, then add 2.0mL of dry acetonitrile and 0.4mmol of 1,4-Cyclohexadiene was placed in a heating device at 60°C and stirred for 12 hours. After the complete reaction was monitored by TLC, the reaction solution was concentrated under reduced pressure, and a mixture of 8:1 petroleum ether and ethyl acetate was used as the mobile phase for column chromatography separation to obtain the corresponding N-phenyl-4-fluorobenzene Sulfonamide 4-Fluoro-N-phenylbenzenesulfonamide Example 1.

[0029] Structural characterization of compound example 1: 1 H NMR (400MHz, Chloroform-d) δ7.81–7.73(m,2H), 7.30–7.21(m,2H), 7.17–7.03(m,5H), 6.72(s,1H). 13 C NMR (...

Embodiment 2

[0031]

[0032] At room temperature, add 0.2mmol of nitrosobenzene, 0.2mmol of sulfur dioxide solid complex DABCO·(SO 2 ) 2 , 0.3mmol p-methoxyphenyltetrafluoroborate diazonium salt, plug the reaction tube with a stopper and place it in high-purity argon to replace the gas, so that the system is in anhydrous and oxygen-free conditions, then add 4.0mL of dichloromethane and 0.2mmol of 1,4-cyclohexadiene was placed in a heating device at 40°C and stirred for 12h. After the complete reaction was monitored by TLC, the reaction solution was concentrated under reduced pressure, and a mixture of 4:1 petroleum ether and ethyl acetate was used as the mobile phase for column chromatography separation to obtain the corresponding N-phenyl-4-methoxy 4-Methoxy-N-phenylbenzenesulfonamide Example 2.

[0033] Structural characterization of compound example 2: 1 H NMR (400MHz, Chloroform-d) δ7.74(d, J=8.1Hz, 2H), 7.23(t, J=7.4Hz, 2H), 7.16(s, 1H), 7.09(d, J=7.6Hz ,3H),6.88(d,J=8.2Hz,2H),...

Embodiment 3

[0035]

[0036] At room temperature, add 0.2mmol p-chloronitrosobenzene, 0.4mmol sulfur dioxide solid complex DABCO·(SO 2 ) 2, 0.5mmol p-tolyl tetrafluoroborate diazonium salt, plug the reaction tube with a stopper and place it in high-purity argon to replace the gas, so that the system is in anhydrous and oxygen-free conditions, then add 2.0mL of dry acetonitrile and 0.6mmol of 1 , 4-cyclohexadiene, placed in a heating device at 30 ° C and stirred for 12 hours. After the complete reaction was monitored by TLC, the reaction solution was concentrated under reduced pressure, and a mixture of 6:1 petroleum ether and ethyl acetate was used as the mobile phase for column chromatography separation to obtain the corresponding N-(4-chlorophenyl) - p-toluenesulfonamide N-(4-chlorophenyl)-4-methylbenzenesulfonamide Example 3.

[0037] Structural characterization of compound example 3: 1 H NMR (400MHz, Chloroform-d) δ7.68(d, J=7.5Hz, 2H), 7.39(s, 1H), 7.24(d, J=7.7Hz, 2H), 7.18(d, ...

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Abstract

The invention belongs to the technical field of organic chemistry, and in particular relates to a preparation method of sulfonamide compounds. The structure of the sulfonamide compounds synthesized by the inventive method 1 H NMR, 13 C NMR characterization and confirmation. The method of the present invention is to react under heating conditions by aryl diazonium salt, sulfur dioxide solid complex and aryl nitroso compound in the presence of a reducing agent in an organic solvent, and form a diazonium salt and sulfur dioxide solid complex The action generates arylsulfonyl free radicals, and then attacks arylnitroso compounds, and the generated hydroxylamine is reduced to obtain sulfonamide compounds. The preparation method of the compound of the present invention has the advantages of mild conditions, simple and efficient, no catalyst, no pre-synthesis of sulfonyl chloride or sodium sulfonate reagents, wide application range of substrates, strong functional group compatibility, easy separation and purification, and excellent industrial performance. and medicinal chemistry application value.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, and in particular relates to a preparation method of sulfonamide compounds. Background technique [0002] Strategies for the synthesis of sulfones and sulfonyls via direct insertion of sulfur dioxide have attracted extensive attention from chemists. Sulfonyl functional groups such as sulfone and sulfonamide widely exist in the backbone of natural products, and some of these compounds have good biological activity and excellent medicinal value. Sulfur dioxide insertion reaction is a simple, efficient, green and environmentally friendly organic synthesis strategy (P.Bisseret, N.Blanchard, Org.Biomol.Chem.2013, 11, 5393; G.Liu, C.Fan, J.Wu, Org. Biomol.Chem.2015,13,1592; J.Zhu,W.-C.Yang,X.-D.Wang,L.Wu,Adv.Synth.Catal.2018,360,386.), its advantage lies in avoiding the traditional The use and preparation of strong acidic sulfonic acid or sulfonyl chloride in the synthesis process of the su...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C303/36C07C311/21C07C311/29C07B45/04
CPCC07C303/36C07B45/04C07C311/21C07C311/29
Inventor 吴劼叶盛青王雪枫
Owner TAIZHOU UNIV
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