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A kind of synthetic method of preparing thiosulfonate based on disproportionation reaction of sodium sulfinic acid

A technology of thiosulfonate and sodium sulfinate, which is applied in the preparation of sulfonic acid amide, chemical instruments and methods, and the preparation of organic compounds, can solve the problems of complex synthesis conditions, etc. The effect of simple process

Active Publication Date: 2021-01-15
SOUTH CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The object of the present invention is to provide a kind of thiosulfonate compound with good biological activity for the deficiencies in the prior art, such as complex synthesis conditions, transition metal catalysis, oxidant (or reducing agent) participation, and use of toxic reagents. (such as broad-spectrum antibacterial, antifungal and antiviral effects), the preparation method of symmetric thiosulfonate and asymmetric thiosulfonate compounds that can be used as organic synthesis reaction intermediates

Method used

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  • A kind of synthetic method of preparing thiosulfonate based on disproportionation reaction of sodium sulfinic acid
  • A kind of synthetic method of preparing thiosulfonate based on disproportionation reaction of sodium sulfinic acid
  • A kind of synthetic method of preparing thiosulfonate based on disproportionation reaction of sodium sulfinic acid

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] With 0.356 grams of sodium p-toluene sulfinate as raw material, the amount of accelerator boron trifluoride diethyl ether is 0.852 grams, and 8 milliliters of dichloromethane as solvent, at a temperature of 50 ° C, react together for 3 hours, through Diluted with water, extracted with dichloromethane, dried over anhydrous sodium sulfate, and separated by column chromatography to obtain 0.245 grams of white solid thiosulfonate product with a yield of 88%. Confirmed by organic matter characterization methods such as spectroscopy and mass spectrometry.

[0023] The structure of product is as follows (the letter mark on the structural formula is corresponding to the label in the nuclear magnetic test data):

[0024]

[0025] Compound characterization data: white solid, m.p.73.8-75.2℃; 1 H NMR (400MHz, CDCl 3 ),δ:2.37(s,3H,ArCH 3 -14),2.42(s,3H,ArCH 3 -13),7.14(d,J=8.0Hz,2H,ArH-9,11),7.21(d,J=8.0Hz,2H,ArH-8,12)7.24(d,J=8.0Hz,2H, ArH-3,5), 7.45 (d, J=8.0Hz, 2H, ArH-2,...

Embodiment 2

[0027] With 0.388 grams of sodium p-methoxybenzene sulfinate as raw material, the amount of accelerator boron trifluoride diethyl ether is 0.852 grams, and 8 milliliters of dichloromethane as solvent, at a temperature of 50 ° C, react together for 3 hours, Diluted with water, extracted with dichloromethane, dried over anhydrous sodium sulfate, and separated by column chromatography to obtain 0.251 g of white solid thiosulfonate product with a yield of 81%. Confirmed by organic matter characterization methods such as carbon spectrum and mass spectrometry.

[0028] The structure of product is as follows (the letter mark on the structural formula is corresponding to the label in the nuclear magnetic test data):

[0029]

[0030] Compound characterization data: white solid, m.p.73.8-75.2℃; 1 HNMR (400MHz, CDCl 3 ),δ:3.82(s,3H,ArCH 3 -14),3.86(s,3H,ArCH 3-13),6.84(d,J=8.0Hz,2H,ArH-3,5),6.87(d,J=8.0Hz,2H,ArH-9,11),7.27(d,J=8.0Hz,2H ,ArH-8,12),7.50(d,J=8.0Hz,2H,ArH-2,6); 13 ...

Embodiment 3

[0032] With 0.441 grams of sodium 2,3,5,6-tetramethylbenzenesulfinate as raw material, the amount of accelerator boron trifluoride diethyl ether is 0.852 grams, 8 milliliters of dichloromethane as solvent, at a temperature of 50 ° C , reacted together for 3 hours, diluted with water, extracted with dichloromethane, dried over anhydrous sodium sulfate, and separated by column chromatography to obtain 0.276 g of white solid thiosulfonate product with a yield of 76%. Confirmed by the characterization methods of organic matter such as hydrogen nuclear magnetic resonance spectrum, carbon nuclear magnetic resonance spectrum, mass spectrometry, and elemental analysis.

[0033] The structure of product is as follows (the letter mark on the structural formula is corresponding to the label in the nuclear magnetic test data):

[0034]

[0035] Compound characterization data: white solid, m.p.135.3-136.8°C; 1 H NMR (400MHz, CDCl 3 ),δ:2.13(s,6H,ArCH 3 -17,20),2.16(s,6H,ArCH 3 -13,1...

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Abstract

The invention relates to a synthetic method for preparing thiosulfonates on the basis of a sulfinic acid sodium salt disproportionated reaction. The preparation method comprises the steps that sulfinic acid sodium salts serve as the raw materials, boron trifluoride diethyl etherate serves as accelerant, dichloromethane serves as solvent, and by means of a disproportionation coupled reaction, a thiosulfinate compound with good biological activity is synthesized; two different sulfinic acid sodium salts serve as the raw materials, and by means of a crossed disproportionation coupled reaction method, an asymmetric thiosulfinate compound can be synthesized. By means of a one-pot method and a two-step method, and by means of a thiosulfonates intermediate prepared on site, a sulfones compound and a sulfonamides compound can be synthesized by directly starting from sulfinic acid sodium salts. Accordingly, a synthetic route for preparing thiosulfonates on the basis of the sulfinic acid sodiumsalt disproportionated reaction is provided for the first time, operation is easy, raw materials are easy to obtain, the condition is mild, no metal catalyst is needed, no additional oxidant or reductant is needed, and the prepared thiosulfonates can have the good biological activity, and can also serve as the intermediate of the reaction to be applied to organic synthesis.

Description

technical field [0001] The present invention relates to the preparation method of symmetrical thiosulfonate and unsymmetrical thiosulfonate. The obtained thiosulfonate has good biological activity and can be further used as an organic synthesis reaction intermediate to synthesize sulfone compounds and sulfone Amide compounds. Background technique [0002] Thiosulfonate is an important class of sulfur-containing organic compounds with good biological activities, such as broad-spectrum antibacterial, antifungal and antiviral effects. In addition, thiosulfonates can also be used as intermediates in organic synthesis reactions. Therefore, the synthesis of thiosulfonate has been receiving people's attention. However, these synthesis methods often require transition metal catalysis and the participation of oxidants or reductants, and when mercaptans are used as raw materials, they have an unpleasant smell, high toxicity, and are easy to poison the catalyst. Therefore, how to sy...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C381/04C07C315/00C07C317/14C07C303/36C07C311/16
CPCC07C303/36C07C315/00C07C381/04C07C2601/02C07C317/14C07C311/16
Inventor 汪朝阳曹梁
Owner SOUTH CHINA NORMAL UNIVERSITY
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