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3-cyclopropyl-N-phenylbenzenesulfonamide and preparation method thereof

A technology of phenylbenzenesulfonamide and cyclopropyl, which is applied in the field of 3-cyclopropyl-N-phenylbenzenesulfonamide and its preparation, can solve the problems of difficult operation, expensive raw materials, low yield and the like, and achieves easy operation. Operation, the effect of high product yield

Inactive Publication Date: 2020-04-10
ZHENGZHOU UNIVERSITY OF LIGHT INDUSTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the synthesis of cyclopropyl benzenesulfonamide compounds is rarely reported in the literature, and the introduction of cyclopropyl substituents reported in the literature is also cumbersome and difficult. Most of them are prepared by ring closure of terminal alkenes, which is not easy to prepare and takes longer steps. , raw materials are expensive, difficult to operate and the yield is not high, etc.
Especially the kind and synthetic method of 3-cyclopropyl-N-phenylbenzenesulfonamide have not yet been found in the literature

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] The preparation method of the 3-cyclopropyl-N-phenylbenzenesulfonamide of the present embodiment is as follows:

[0018] (1) Synthesis of 3-bromo-N-phenylbenzenesulfonamide

[0019] Take a 100ml single-necked bottle, add 4.74g (0.02mol) of 3-bromobenzenesulfonic acid, and add 100mL of pyridine, stir to dissolve, then add 1.86g (0.02mol) of aniline, and then slowly add the condensing agent EDC to the reaction solution in batches -HCl 5.73g (0.03mol), then heated to 50°C to react for 2h, rotary evaporated to remove pyridine, poured the remaining water into the separatory funnel, added an appropriate amount of ethyl acetate to it for extraction 3 times, and used the ethyl acetate layer Wash once with dilute hydrochloric acid water, combine the organic layers, dry the organic layer with anhydrous sodium sulfate, and remove the solvent under reduced pressure to obtain 5.3 g of white solid, with a yield of 85%;

[0020] MS: m / z: [M+1]: 311.9, 313.9.

[0021] 1 H NMR (400 M...

Embodiment 2

[0031] The preparation method of the 3-cyclopropyl-N-phenylbenzenesulfonamide of the present embodiment is as follows:

[0032] (1) Synthesis of 3-bromo-N-phenylbenzenesulfonamide

[0033] Take a 100ml single-necked bottle, add 4.74g (0.02mol) of 3-bromobenzenesulfonic acid, and add 100mL of pyridine, stir to dissolve, then add 2.04g (0.022mol) of aniline, and then slowly add the condensing agent EDC to the reaction solution in batches -HCl 5.73g (0.03mol), then heated to 50°C to react for 2h, rotary evaporated to remove pyridine, poured the remaining water into the separatory funnel, added an appropriate amount of ethyl acetate to it for extraction 3 times, and used the ethyl acetate layer Washed once with dilute hydrochloric acid water, combined the organic layers, dried the organic layer with anhydrous sodium sulfate, and removed the solvent under reduced pressure to obtain 5.49 g of white solid, with a yield of 88%;

[0034] (2) Synthesis of 3-cyclopropyl-N-phenylbenzenes...

Embodiment 3

[0037] The preparation method of the 3-cyclopropyl-N-phenylbenzenesulfonamide of the present embodiment is as follows:

[0038] (1) Synthesis of 3-bromo-N-phenylbenzenesulfonamide

[0039] Take a 100ml single-necked bottle, add 4.74g (0.02mol) of 3-bromobenzenesulfonic acid, and add 100mL of pyridine, stir to dissolve, then add 2.23g (0.024mol) of aniline, and then slowly add the condensing agent EDC to the reaction solution in batches -HCl 5.73g (0.03mol), then heated to 50°C to react for 2h, rotary evaporated to remove pyridine, poured the remaining water into the separatory funnel, added an appropriate amount of ethyl acetate to it for extraction 3 times, and used the ethyl acetate layer Wash once with dilute hydrochloric acid water, combine the organic layers, dry the organic layer over anhydrous sodium sulfate, and remove the solvent under reduced pressure to obtain 5.55 g of white solid, with a yield of 89%;

[0040] (2) Synthesis of 3-cyclopropyl-N-phenylbenzenesulfona...

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Abstract

The invention discloses 3-cyclopropyl-N-phenylbenzenesulfonamide and a preparation method thereof. The preparation method comprises the following steps: dissolving 3-bromobenzenesulfonic acid and aniline in pyridine, then adding a condensing agent EDC-HCl, and carrying out a reaction for 2 to 3 h at a temperature of 50 to 80 DEG C so as to obtain 3-bromo-N-phenylbenzenesulfonamide; dissolving 3-bromo-N-phenylbenzenesulfonamide into a dioxane solution; adding cyclopropylboronic acid, sodium carbonate, an aqueous solution and Pd (dppf) Cl2, reacting a mixed system at 110 DEG C for 8-10 hours ina nitrogen atmosphere, and carrying out aftertreatment to obtain 3-cyclopropyl-N-phenylbenzenesulfonamide. The preparation method has the advantages of relatively mild conditions, easy product treatment and purification and suitability for batch preparation. The preparation method provided by the invention is easy to operate in reaction, high in product yield and suitable for batch preparation, sothat the preparation method of 3-cyclopropyl-N-phenylbenzenesulfonamide has an important application value.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to 3-cyclopropyl-N-phenylbenzenesulfonamide and a preparation method thereof. Background technique [0002] Sulfonamide compounds have very diverse pharmacological activities, such as strong antihypertensive, antiarrhythmic, antithrombotic activities, etc. Many drug molecules and natural products contain sulfonamide structures or fragments, so sulfonamide derivatives are important pharmaceutical intermediates. However, the synthesis of cyclopropyl benzenesulfonamide compounds is rarely reported in the literature, and the introduction of cyclopropyl substituents reported in the literature is also cumbersome and difficult. Most of them are prepared by ring closure of terminal alkenes, which is not easy to prepare and takes longer steps. , raw materials are expensive, difficult to operate and the yield is not high. In particular, no literature reports have been f...

Claims

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Application Information

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IPC IPC(8): C07C311/21C07C303/40
CPCC07C303/38C07C303/40C07C311/21C07C2601/02
Inventor 闫福丰王世卓王旭哲
Owner ZHENGZHOU UNIVERSITY OF LIGHT INDUSTRY