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Sulfonyl pyridine amide derivatives and preparation method thereof

A technology for sulfonylpyridine amide and derivatives, which is applied in the field of sulfonylpyridine amide derivatives and their preparation, can solve the problems of limited practicability due to reaction conditions, and achieve the effect of promoting industrialization and high-efficiency circulation

Active Publication Date: 2022-03-18
HANGZHOU VOCATIONAL & TECHN COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the presence of noble metals and toxic transition metals, harsh reaction conditions, and high catalytic loading greatly limit the practicality of these methods

Method used

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  • Sulfonyl pyridine amide derivatives and preparation method thereof
  • Sulfonyl pyridine amide derivatives and preparation method thereof
  • Sulfonyl pyridine amide derivatives and preparation method thereof

Examples

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preparation example Construction

[0046] Preparation of Chitosan-supported Copper-Carbon Nanocatalysts

[0047] In a 100 mL round bottom flask equipped with a reflux condenser and a magnetic stir bar, anhydrous copper acetate (90.83 mg, 0.500 mmol) was dissolved in H 2 O (40mL). Chitosan (690 mg) was then added to the solution to obtain a suspension which was stirred at 50 °C for 3 h. After the solution was cooled to room temperature, the H was slowly removed by suction filtration under reduced pressure. 2 O, the filter cake was washed three times with ethanol and water to give a light blue solid. The light blue solid obtained was dried at 60° C. under vacuum for 12 hours. The dried samples were evenly transferred into porcelain boats and then put into a tube furnace. The tube furnace was evacuated and then flushed with nitrogen for half an hour. Keep nitrogen flowing in the tube furnace, heat the tube furnace to 200 °C with a temperature gradient of 2 °C / min, and keep it in nitrogen atmosphere for 2 hour...

Embodiment 1

[0049] The preparation of N-(2-ethylphenyl) pyridine-2-carboxamide (R in structural formula II 1 is pyridyl, R 2 Ortho-substituted ethyl)

[0050]In a 150mL round-bottomed flask, add 2-pyridinium formate (12mmol, 1.48g), 2-ethylaniline (10mmol, 1.21g) and 50mL of dichloromethane (DCM), stir in an ice bath, and then pour into the round-bottomed flask DCM solution mixed with dicyclohexylcarbodiimide (DCC) (15mmol, 3.1g) and 4-dimethylaminopyridine (DMAP) (5mmol, 0.61g) was added dropwise, and the reaction was continued at room temperature after the dropwise addition was completed. Hours, the reaction was checked by TLC. After the reaction is completed, the reaction solution is suction-filtered, the filtrate is collected, spin-dried, and the eluent is purified through the column with the ratio of petroleum ether and ethyl acetate (25:1), and N-(2-ethyl phenyl)pyridine-2-carboxamide.

[0051] The preparation of pyridine-3-sodium sulfinate (R in the formula III 3 for meta-subs...

Embodiment 2

[0061] The preparation of N-(2-methoxyphenyl) pyridine-2-carboxamide (R in structural formula II 1 is pyridyl, R 2 for ortho methoxy)

[0062] In a 150mL round bottom flask, add 2-pyridinium formate (12mmol, 1.48g), 2-methoxyaniline (10mmol, 1.23g) and 50mL of dichloromethane (DCM), stir under ice bath, and then pour A DCM solution mixed with dicyclohexylcarbodiimide (DCC) (15mmol, 3.1g) and 4-dimethylaminopyridine (DMAP) (5mmol, 0.61g) was added dropwise in the flask, and the reaction was continued at room temperature after the addition was complete After 6 hours, the reaction was checked by TLC. After the reaction is completed, the reaction solution is suction-filtered, the filtrate is collected, spin-dried, and the eluent is purified by column with the ratio of petroleum ether and ethyl acetate (25:1), and N-(2-methoxy phenyl)pyridine-2-carboxamide.

[0063] The preparation of N-[4-(benzenesulfonyl)-2-methoxyphenyl]pyridine-2-carboxamide (R in structural formula I 1 is...

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Abstract

The invention relates to a sulfonyl pyridine amide derivative and a preparation method thereof. The compound represented by the structural formula (II), the compound represented by the structural formula (III), an oxidizing agent, an additive, and a heterogeneous biomass-supported copper catalyst are added to a reaction vessel , adding a solvent, and stirring the reaction at room temperature; after the reaction is completed, filter, extract, concentrate, separate and purify to obtain the sulfonyl pyridine amide derivatives shown in structural formula (I). The synthesis method of the sulfonylpyridine amide derivatives provided by the invention is scientific and reasonable, and a series of sulfonyl pyridine amide derivatives are synthesized by a green and efficient synthesis method by using a heterogeneous biomass-supported copper catalyst to catalyze the reaction.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a sulfonyl pyridine amide derivative and a preparation method thereof. Background technique [0002] Arylamines are common and basic industrial raw materials, which are widely used in agriculture, materials and pharmaceutical synthesis. Sulfur-containing compounds are important components of natural products, functional materials and drugs, such as the herbicide mesotrione, the anti-migraine drugs sumatriptan and eletriptan, etc., and their structural formulas are as follows: [0003] [0004] They play an important role in biology and medicine, so it is necessary to continuously explore more efficient and concise C-S bond formation methods. [0005] Typical methods for the synthesis of sulfones include oxidation of sulfides, alkylation of sulfinates, Friedel-Crafts-type sulfonation of arenes, and electrophilic substitution of arenes with sulfonyl halid...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/81C07D215/48C07D217/26C07D401/12B01J31/06
CPCC07D213/81C07D215/48C07D217/26C07D401/12B01J31/06B01J2231/4294
Inventor 于文博朱军陈郁冯海霞
Owner HANGZHOU VOCATIONAL & TECHN COLLEGE
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