Method for synthesizing vinyl sulfone compound

A synthesis method and compound technology are applied in the preparation of organic compounds, chemical instruments and methods, organic compounds/hydrides/coordination complex catalysts, etc., and can solve the problems of poor economy, high price, and difficulty in handling, etc. Achieving the effect of broad reaction substrate, reduced reaction cost and high reaction efficiency

Inactive Publication Date: 2017-09-19
TONGJI UNIV
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Problems solved by technology

[0003] In recent years, with the deepening of the application of visible light catalysis in organic synthesis, the research on the synthesis of similar compounds by visible light catalysis has also been reported first. The photocatalysts used in these works are metal ruthenium (II) and iridium ((III) Such metal complexes are expensive and difficult to handle, so the economy is not good

Method used

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  • Method for synthesizing vinyl sulfone compound
  • Method for synthesizing vinyl sulfone compound
  • Method for synthesizing vinyl sulfone compound

Examples

Experimental program
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Effect test

Embodiment 1

[0029] In the dry reaction tube, add 0.2mmol of p-toluenesulfonyl chloride, 1.0mmol of triethylamine, 3%mmol of Eosin Y, 0.6mmol K 2 HPO 4 , And then add 6mL of C 2 H 5 OH / CH 3 COCH 3 (1:2), under the 3W blue LED light, react for 2h in the air at room temperature. After the reaction, wash with water, extract, dry, and then remove the organic solvent under reduced pressure. The product undergoes thin layer chromatography and column chromatography ( Petroleum ether / ethyl acetate = 5 / 1). The resulting product yield is 67%.

[0030] (E)-N,N-diethyl-2-tosylethenamine

[0031] Brown oil.

[0032] 1 H NMR(400MHz, CDCl 3 ): δ7.75(d,J=8.2Hz,2H), 7.31(d,J=12.7Hz,1H), 7.27(d,J=8.0Hz,2H), 4.91(d,J=12.7Hz,1H ), 3.18 (broad doublet, 4H), 2.41 (s, 3H), 1.17 (bs, 6H).

[0033] 13 C NMR(100MHz, CDCl 3 )δ148.5, 142.3, 141.8, 128.5, 125.9, 91.4, 49.8(bs), 42.4(bs), 21.2, 14.5(bs)11.0(bs).

[0034] HRMS(ESI):calcd for C 13 H 19 O 2 NS+Na=276.1020,found:276.1029.

Embodiment 2

[0036] In the dry reaction tube, add 0.2mmol of benzenesulfonyl chloride, 1.0mmol of triethylamine, 3%mmol of Eosin Y, 0.6mmol K 2 HPO 4 , And then add 6mL of C 2 H 5 OH / CH 3 COCH 3 (1:2), irradiated by 3W blue LED lamp, react for 2h in the air at room temperature. After the reaction, wash with water, extract, dry and then remove the organic solvent under reduced pressure. The product is subjected to thin layer chromatography and column chromatography ( Petroleum ether / ethyl acetate = 5 / 1). The resulting product yield is 65%.

[0037] (E)-N,N-Diethyl-2-(phenylsulfonyl)ethenamine

[0038] White solid.

[0039] mp 45-46℃; 1 H NMR(400MHz, CDCl 3 )δ7.92-7.86(m,2H),7.5-7.47(m,3H), 7.35(d,J=12.7Hz,1H), 4.94(d,J=12.7Hz,1H), 3.22(broad doublet, 4H), 1.19 (broaddoublet, 6H).

[0040] 13 C NMR(100MHz, CDCl 3 )δ148.9, 145.2, 131.3, 128.6, 125.8, 91.0, 49.8(bs), 42.5(bs), 14.5(bs), 10.9(bs).

[0041] HRMS(ESI):calcd for C 12 H 17 O 2 NS+Na=257.1324, found: 257.1318.

Embodiment 3

[0043] In the dry reaction tube, add 0.2mmol of p-methoxybenzenesulfonyl chloride, 1.0mmol of triethylamine, 3%mmol of Eosin Y, 0.6mmol K 2 HPO 4 , And then add 6mL of C 2 H 5 OH / CH 3 COCH 3 (1:2), under the 3W blue LED light, react for 2h in the air at room temperature. After the reaction, wash with water, extract, dry, and then remove the organic solvent under reduced pressure. The product undergoes thin layer chromatography and column chromatography ( Petroleum ether / ethyl acetate = 5 / 1). The resulting product yield is 63%.

[0044] (E)-N,N-diethyl-2-(4-methoxyphenylsulfonyl)ethenamine

[0045] Brown oil.

[0046] 1 H NMR(400MHz, CDCl 3 )δ7.81(d,J=8.9Hz,2H), 7.31(d,J=2.5Hz,1H), 6.97(d,J=8.9Hz,2H), 4.92(d,J=12.7Hz,1H) ,3.88(s,3H), 3.20(broad doublet, 4H), 1.18(bs,6H).

[0047] 13 C NMR(100MHz, CDCl 3 )δ161.8, 148.2, 137.1, 127.9, 113.7, 91.8, 5.3, 49.7(bs), 42.1(bs), 14.4(bs), 11.0(bs).

[0048] HRMS(ESI):calcd for C 13 H 19 O 3 NS+Na=292.1005,found:292.0978.

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Abstract

The invention relates to a method for synthesizing a vinyl sulfone compound. The vinyl sulfone compound has a chemical molecular formula shown in the description, wherein R1 is one selected from H, a straight-chain alkyl electron-donating group, a nitro electron withdrawing group, F, Cl and Br, and R2, R3 and R4 each is selected from H and straight-chain alkyl. The synthetic method comprises the steps of adding an inorganic base in an organic reaction solvent by taking an aryl sulfonyl chloride compound and a tertiary amine compound as reaction substrates and taking eosin Y as a catalyst under the action of visible light, carrying out a reaction for 1 to 3 hours at the temperature of -5 DEG C to 5 DEG C under the irradiation of an LED (light-emitting diode) lamp, carrying out water washing treatment, extraction and drying after the reaction ends, then, carrying out reduced-pressure distillation to remove the organic solvent, and then, carrying out thin-layer chromatography and column chromatography separation, thereby preparing the vinyl sulfone compound. Compared with the prior art, the method provided by the invention has the advantages that the steps are simple, the reaction conditions are mild, the controllability is good, the consumption of metal complexes is avoided, the reaction cost is reduced, and the method is pollution-free to environments.

Description

Technical field [0001] The invention belongs to the technical field of organic synthesis and relates to a method for synthesizing sulfone compounds. Background technique [0002] Disulfone compounds have a unique chemical structure and are important organic synthesis intermediates, which are widely used in the fields of organic synthesis and medicinal chemistry. Vinylsulfone is an excellent Micheal receptor and can be used as a neuroprotective agent to treat Parkinson's disease. Further research found that vinyl sulfone compounds can be used as inhibitors of cysteine ​​protease. The synthesis of such compounds has also been extensively studied. [0003] In recent years, as the application of visible light catalysis in organic synthesis has continued to deepen, there have been previous reports on the use of visible light catalysis to synthesize similar compounds. The photocatalysts used in these works are metal ruthenium (II) and iridium ((III) Other metal complexes are expensive...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C315/00C07C317/28B01J31/04
CPCB01J31/04C07C315/00C07C317/28
Inventor 蔡雨国张荣华
Owner TONGJI UNIV
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