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Method for preparing sulfone compound by utilizing electrochemical micro-channel technology

A compound and electrochemical technology, applied in the field of preparation of sulfone compounds using electrochemical microchannel synthesis technology, can solve the problems of highly toxic residues in products, high preparation costs, and engineering scale-up, and achieve fast reaction speed, high acidification degree, high efficiency effect

Active Publication Date: 2019-08-09
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The technical problem to be solved by the present invention is to provide a method for preparing sulfone compounds by using electrochemical microflow field reaction technology to solve the problem of high preparation cost in the preparation of sulfone compounds in the prior art. , low efficiency, difficult engineering scale-up, and the product contains highly toxic residues and other problems

Method used

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  • Method for preparing sulfone compound by utilizing electrochemical micro-channel technology
  • Method for preparing sulfone compound by utilizing electrochemical micro-channel technology
  • Method for preparing sulfone compound by utilizing electrochemical micro-channel technology

Examples

Experimental program
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Effect test

Embodiment 1

[0032]

[0033] Weigh compound IA (4mmol, 1.0equiv), with 10mL CH 3 CN / DCE (v / v=9 / 1) was dissolved and loaded into syringe 1 after complete dissolution. Weigh 4-methylbenzenesulfinic acid (12mmol, 3.0equiv), n Bu 4 NBF 4 (6.0mmol) with 10mL CH 3CN / DCE (v / v=9 / 1) was dissolved and loaded into syringe 2 after complete dissolution. After exhausting the air in the syringe, push it into the micro-mixer 1 through the syringe pump at a flow rate of 1.0mL / min. After being mixed by the mixer, pump it into the coil with an inner diameter of 0.5mm. Two graphite SK-50 electrodes are used as cathode and anode In the electrochemical microchannel reaction device, the constant current is 10mA. The reaction was carried out at room temperature with a residence time of 4 min. After the reaction was completed, it was tracked and monitored by TLC. The solution was washed with saturated NaHCO 3 The solution was quenched and the aqueous layer was washed with CH 2 Cl 2 (3 x 10 mL) extract...

Embodiment 2

[0035]

[0036] Weigh compound IA (4mmol, 1.0equiv), with 10mL CH 3 CN / DCE (v / v=9 / 1) was dissolved and loaded into syringe 1 after complete dissolution. Weigh 4-methylbenzenesulfinic acid (12mmol, 3.0equiv), n Bu 4 NBF 4 (6.0mmol) with 10mL CH 3 CN / DCE (v / v=9 / 1) was dissolved and loaded into syringe 2 after complete dissolution. After exhausting the air in the syringe, push it into the micro-mixer 1 through the syringe pump at a flow rate of 1.0mL / min. After being mixed by the mixer, pump it into the coil with an inner diameter of 0.5mm. Two graphite SK-50 electrodes are used as cathode and anode In the electrochemical microchannel reaction device, the constant current is 30mA. The reaction was carried out at room temperature with a residence time of 4 min. After the reaction was completed, it was tracked and monitored by TLC. The solution was washed with saturated NaHCO 3 The solution was quenched and the aqueous layer was washed with CH 2 Cl 2 (3 x 10 mL) extrac...

Embodiment 3

[0038]

[0039] Weigh compound IA (4mmol, 1.0equiv), with 10mL CH 3 CN / DCE (v / v=9 / 1) was dissolved and loaded into syringe 1 after complete dissolution. Weigh 4-methylbenzenesulfinic acid (12mmol, 3.0equiv), n Bu 4 NBF 4 (6.0mmol) with 10mL CH 3 CN / DCE (v / v=9 / 1) was dissolved and loaded into syringe 2 after complete dissolution. After exhausting the air in the syringe, push it into the micro-mixer 1 through the syringe pump at a flow rate of 1.0mL / min. After being mixed by the mixer, pump it into the coil with an inner diameter of 0.5mm. Two graphite SK-50 electrodes are used as cathode and anode In the electrochemical microchannel reaction device, the constant current is 1mA. The reaction was carried out at room temperature with a residence time of 4 min. After the reaction was completed, it was tracked and monitored by TLC. The solution was washed with saturated NaHCO 3 The solution was quenched and the aqueous layer was washed with CH 2 Cl 2 (3 x 10 mL) extract...

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Abstract

The invention discloses a method for preparing a sulfone compound by utilizing an electrochemical micro-channel technology. A compound I is dissolved with an acetonitrile and dichloroethane mixed solvent, and the mixture is loaded in an injector 1 after being completely dissolved; 4-methyl benzenesulfinate and electrolyte are dissolved with an acetonitrile and dichloroethane mixed solvent, and themixture is loaded into an injector 2 after being completely dissolved; the materials in the injector 1 and the materials in the syringe 2 are pumped into a micro-mixer of a micro-channel reaction device at the same time to be mixed, and the materials are completely mixed and then pumped into the electrochemical micro-channel reaction device, react under a constant current and are oxidized to obtain the sulfone compound. The method has the advantages that the method is safe and environmentally friendly, the raw materials are low in price and easy to obtain, highly toxic reactant residues are avoided, the reaction speed is high and the efficiency is high; a sulfone compound product prepared through the preparation method has the advantages of high purity, high acidification degree and the like, and is suitable for large-scale preparation.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a method for preparing sulfone compounds by using electrochemical microchannel synthesis technology. Background technique [0002] Sulfone compounds are an important class of organic synthesis intermediates, which are widely used in chemistry, medicine, pesticides and materials science, and have certain biological activities. For example, a variety of aryl sulfones have shown good pharmacological activities such as antifungal, antibacterial, anticancer, anti-AIDS, anti-leprosy, and anti-leishmania); aryl sulfones have also been found in COX-2 inhibitors; in addition , recent studies have found that α, β-unsaturated sulfone can be used as an inhibitor of induction of VCAM-1 (vascular cell adhesion molecule-1); vinyl sulfone is an intermediate of many new dyes. In addition, the sulfonyl functional group is easy to introduce and remove under mild conditions. The introd...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C25B3/02C25B3/23
CPCC25B3/23
Inventor 郭凯庄恺强郑明卫袁鑫崔玉声覃龙州邱江凯
Owner NANJING UNIV OF TECH
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