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A kind of method of synthesizing sulfoxide compound

A compound and sulfoxide technology, applied in the field of organic compound synthesis, can solve the problems of harsh reaction conditions and low metal-containing waste, and achieve the effects of high reaction efficiency, high atom utilization rate, and wide application range of substrates

Active Publication Date: 2021-01-29
南京雷正医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, many reactions in these systems still require harsh reaction conditions with metal-containing wastes and low selectivities

Method used

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  • A kind of method of synthesizing sulfoxide compound
  • A kind of method of synthesizing sulfoxide compound
  • A kind of method of synthesizing sulfoxide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] The preparation of embodiment 1 benzyl phenyl sulfoxide

[0044]

[0045] In a dry Shrek reaction tube, add benzylphenyl sulfide (0.25 mmol) sulfide and PDI (0.5 mol%), PDI is the compound of formula A in methanol (2.0 mL). Next, fill a balloon with oxygen and fix it on top of the Shrek reaction tube. Under normal pressure oxygen atmosphere, irradiated with 15W white CFL to react at room temperature. After the reaction was complete, brine was added to the reaction. The aqueous phase was re-extracted with ethyl acetate. Synthetic organic extracts in Na 2 SO 4 Drying and concentrating in vacuo, the resulting residue was separated by silica gel column chromatography (petroleum ether: ethyl acetate = 10:1), and purified to obtain a white viscous solid (yield: 95%; selectivity: 100%). 1 H NMR (400MHz, CDCl 3 ): δppm 7.47-7.36(m,5H,ArH),7.29-7.21(m,3H,ArH),6.98-6.96(m,2H,ArH),4.00-3.97(m,2H,CH 2 ).

Embodiment 2

[0046] The preparation of embodiment 2 benzhydryl sulfoxide

[0047]

[0048] In a dry Shrek reaction tube, add benzhydryl sulfide (0.25 mmol) sulfide and PDI (0.5 mol%), PDI is the compound of formula B in methanol (2.0 mL). Next, fill a balloon with oxygen and fix it on top of the Shrek reaction tube. Under normal pressure oxygen atmosphere, irradiated with 15W white CFL to react at room temperature. After the reaction was complete, brine was added to the reaction. The aqueous phase was re-extracted with ethyl acetate. Synthetic organic extracts in Na 2 SO 4 Drying and concentration in vacuo, the resulting residue was separated by silica gel column chromatography (petroleum ether: ethyl acetate = 10:1), and purified to obtain a white viscous solid (yield: 90%; selectivity: 100%). 1 H NMR (400MHz, CDCl 3 ): δppm 7.40-7.34(m,3H,ArH),7.30-7.28(m,2H,ArH),3.94-3.86(m,2H,CH 2 ).

Embodiment 3

[0049] The preparation of embodiment 3 methyl phenyl sulfoxide

[0050]

[0051] In a dry Shrek reaction tube, methyl phenyl sulfide (0.25 mmol) sulfide and PDI (0.5 mol%), the compound of formula A, were added in methanol (2.0 mL). Next, fill a balloon with oxygen and fix it on top of the Shrek reaction tube. Under normal pressure oxygen atmosphere, irradiated with 15W white CFL to react at room temperature. After the reaction was complete, brine was added to the reaction. The aqueous phase was re-extracted with ethyl acetate. Synthetic organic extracts in Na 2 SO 4 Drying and concentration in vacuo, the resulting residue was separated by silica gel column chromatography (petroleum ether: ethyl acetate = 10:1), and purified to obtain a white viscous solid (yield: 94%; selectivity: 100%). 1 H NMR (400MHz, CDCl 3 ): δppm 7.67-7.64(m,2H,ArH),7.56-7.48(m,3H,ArH),2.73(s,3H,CH 3 ).

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Abstract

The invention discloses a method for synthesizing sulfoxide compounds, belonging to the technical field of organic compound synthesis. The method of the invention comprises: using perylene imide as a catalyst to catalyze the reaction of the sulfide compound and the oxygen agent under light conditions to obtain the sulfoxide compound. The present invention realizes the selective oxidation of thioether catalyzed by peryleneimide under visible light for the first time, and successfully constructs sulfoxide suborganisms with high yield; the present invention has mild reaction conditions, high reaction efficiency, wide application range of substrates, and high atom utilization rate High, reflecting high regioselectivity and chemoselectivity, which has potential application value.

Description

technical field [0001] The invention specifically relates to a method for synthesizing sulfoxide compounds, which belongs to the technical field of organic compound synthesis. Background technique [0002] The selective oxidation of organic compounds is one of the most fundamental reactions in organic synthesis and one of the most critical challenges in industrial chemistry. Traditionally, toxic or hazardous oxidizing agents, such as toxic metal oxides and peroxides, are usually used in stoichiometric quantities for these chemical transformations. Owing to the growing concern about environmental issues, extensive efforts have been made to develop cleaner synthetic strategies utilizing oxygen as the most economical and greenest terminal oxidant. However, due to the triplet ground-state structure of oxygen, it is inactive and difficult to be activated, especially for inert C-H bonds. To overcome its high oxidation potential, expensive and toxic noble metal catalysts, or poro...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C315/02C07C317/10C07C317/14C07C317/22C07C317/04B01J31/02
CPCB01J31/0244C07C315/02C07C2601/02C07C317/10C07C317/14C07C317/22C07C317/04
Inventor 范文华许桓范为正张艳
Owner 南京雷正医药科技有限公司
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