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A kind of vulcanization method of nitrogen-containing heterocycle substituted pyrrole derivative

A technology of pyrrole derivatives and nitrogen heterocycles, which is applied in organic chemistry and other fields, can solve problems such as unfavorable preparation, harsh reaction conditions, and metal ion residues, and achieve the effects of mild reaction conditions, good compatibility, and high yield

Active Publication Date: 2021-05-25
CHANGZHOU VOCATIONAL INST OF ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the prior art, literature (Synthesis, 2019, 51, 545–551) and patent CN107698558 report the method of catalytically synthesizing nitrogen-containing heterocycle-substituted aryl sulfide compounds at high temperature using transition metal copper salts and organic ligands. However, the harsh reaction conditions may easily lead to residual metal ions in the product, which is not conducive to mass production

Method used

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  • A kind of vulcanization method of nitrogen-containing heterocycle substituted pyrrole derivative
  • A kind of vulcanization method of nitrogen-containing heterocycle substituted pyrrole derivative
  • A kind of vulcanization method of nitrogen-containing heterocycle substituted pyrrole derivative

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Embodiment 1

[0024] Adopt the method of the present invention to synthesize 2-(2,5-bis(propylthio)-1H-pyrrol-1-yl)pyridine, its reaction formula is:

[0025]

[0026] The specific synthesis steps are: put 2-(1H-pyrrol-1-yl)pyridine (0.72g, 5mmol) and dipropyl disulfide (1.65g, 11mmol) in a reaction flask, add iodine (0.13g, 0.5mmol ), potassium phosphate (2.1g, 10mmol) and 10mL dimethyl sulfoxide, heated to 80°C for 6 hours, the reaction was complete as monitored by thin-layer chromatography, added 30mL of water and 20mL of ethyl acetate for extraction, and the organic layer was sequentially washed with saturated saline Washing, drying over anhydrous sodium sulfate, concentration to obtain an oily substance, and purification by column chromatography gave 1.28 g of a colorless oily substance (target product), with a yield of 87.2% (based on 2-(1H-pyrrol-1-yl)pyridine), For the NMR spectrum of the target product, see figure 2 , the NMR data are as follows:

[0027] 1 H NMR (300MHz, DM...

Embodiment 2

[0029] Adopt the method of the present invention to synthesize 2-(2,5-bis(propylthio)-1H-pyrrol-1-yl)pyridine, the specific synthesis steps are: 2-(1H-pyrrol-1-yl)pyridine (0.72g , 5mmol) and dipropyl disulfide (1.5g, 10mmol) were placed in a reaction flask, and iodine (0.13g, 0.5mmol), potassium carbonate (1.4g, 10mmol) and 15mL N,N-dimethylformamide were added , heated to 100°C and reacted for 6 hours, the reaction was complete as monitored by thin-layer chromatography, and extracted by adding 30 mL of water and 20 mL of ethyl acetate, wherein the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated to obtain an oily substance, which was purified by column chromatography 1.0 g of a colorless oil (the target product) was obtained with a yield of 68.5% (calculated as 2-(1H-pyrrol-1-yl)pyridine).

Embodiment 3

[0031] Adopt the method of the present invention to synthesize 2-(2,5-bis(propylthio)-1H-pyrrol-1-yl)pyridine, the specific synthesis steps are: 2-(1H-pyrrol-1-yl)pyridine (0.72g , 5mmol) and dipropyl disulfide (2.25g, 15mmol) were placed in a reaction flask, and iodine (0.13g, 0.5mmol), potassium bicarbonate (1.5g, 15mmol) and 15mL of 1,2-dichloroethane were added , heated to 60°C for 12 hours, the reaction was complete as monitored by thin-layer chromatography, concentrated, added 30 mL of water and 20 mL of ethyl acetate for extraction, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated to obtain an oily substance. Analysis and purification gave 0.82 g of a colorless oil (the target product), with a yield of 56.2% (based on 2-(1H-pyrrol-1-yl)pyridine).

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Abstract

The invention discloses a vulcanization method of pyrrole derivatives substituted by nitrogen-containing heterocycles. The method uses nitrogen-containing heterocycles substituted pyrrole derivatives and vulcanization reagents as reaction raw materials, and catalyzes the synthesis in an organic solvent where iodine simple substance and inorganic base exist. Disubstituted nitrogen-containing heterocyclic aryl sulfide compounds, the method does not require the use of transition metal catalysts, avoids high-temperature reaction conditions, has the characteristics of simple operation steps, environmental protection, good compatibility with substrates, and high yields. It is suitable for the industrial production of disubstituted nitrogen-containing heterocyclic substituted aryl sulfide compounds.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry, and in particular relates to a vulcanization method of pyrrole derivatives substituted by nitrogen-containing heterocyclic rings. Background technique [0002] Arylsulfide compounds substituted by nitrogen-containing heterocycles are an important class of intermediates, which are widely used in the fields of medicine, pesticides, and chemicals. In the prior art, literature (Synthesis, 2019, 51, 545–551) and patent CN107698558 report the method of catalytically synthesizing nitrogen-containing heterocycle-substituted aryl sulfide compounds at high temperature using transition metal copper salts and organic ligands. However, the harsh reaction conditions easily lead to residual metal ions in the product, which is not conducive to mass production. Therefore, it is of great significance to develop a method with high economical practicability, mild reaction conditions, readily ava...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/04C07D403/04
CPCC07D401/04C07D403/04
Inventor 周海平翁智兵贺新
Owner CHANGZHOU VOCATIONAL INST OF ENG