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A kind of preparation method of thiosulfonate compound in aqueous phase

A technology for thiosulfonate and compounds, which is applied in the field of preparing thiosulfonate compounds, can solve problems such as high reaction temperature, and achieve the effect of easy purification and simple operation

Active Publication Date: 2020-11-10
NINGBO UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The inventor (Synlett, 29 (2018), 2076-2080) reported a method (formula 3) for preparing thiosulfonate compounds from sulfonyl hydrazide, which also requires the use of toxic organic solvent tetrahydrofuran (THF) As a reaction solvent and the reaction temperature is higher

Method used

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  • A kind of preparation method of thiosulfonate compound in aqueous phase
  • A kind of preparation method of thiosulfonate compound in aqueous phase
  • A kind of preparation method of thiosulfonate compound in aqueous phase

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028]

[0029] Add sulfonyl hydrazide (39.2 mg, 0.2 mmol), tetrabutylammonium iodide (TBAI, 14.8 mg, 0.04 mmol), tert-butanol peroxide (t-BuOOH, 21.6 mg, 0.24mmol), and then add solvent water (2mL), and then stir the reaction in the reactor at 40°C under air atmosphere. The reaction progress is monitored by TLC until the raw materials disappear (reaction time is 24 hours). After the reaction is completed, the reaction solution It was extracted three times with ethyl acetate, the organic phase was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to remove the solvent, and the residue was separated by column chromatography (elution solvent: ethyl acetate / n-hexane) to obtain the target product I- 1. (83% yield); 1 H NMR (400MHz, DMSO-d6) δ: 7.45 (d, J = 7.6 Hz, 2H), 7.38 (d, J = 7.6 Hz, 2H), 7.26-7.20 (m, 4H), 2.40 (s, 3H) , 2.34(s, 3H); 13 C NMR (100MHz, DMSO-d6) δ: 145.6, 142.6, 140.1, 136.5, 130.9, 130.3, 127.6, 124.2, 21.6, 21.4.

Embodiment 2

[0031] Use accelerator iodine elemental (I 2 , 10.1 mg, 0.04 mmol) instead of tetrabutylammonium iodide, and other conditions are the same as in Example 1, and the yield of the target product I-1 is 40%.

Embodiment 3

[0033] The accelerator potassium iodide (KI, 6.6 mg, 0.04 mmol) was used instead of tetrabutylammonium iodide, and the remaining conditions were the same as in Example 1, and the yield of the target product I-1 was 12%.

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Abstract

The invention relates to a preparation method of thiosulfonate compounds in water phase. In the method, sulfonyl hydrazide, accelerator, oxidizing agent and solvent water are added into a Schlenk reaction bottle, stirred and reacted under certain temperature and air atmosphere conditions, and thiosulfonate compounds are obtained through free radical coupling reaction.

Description

Technical field [0001] This application belongs to the field of organic synthesis, and specifically relates to a method for preparing thiosulfonate compounds in an aqueous phase using sulfonyl hydrazine as a raw material, with simple process, low cost, and environment-friendly method. Background technique [0002] Thiosulfonate compounds are not only the core skeleton of various drug molecules with antibacterial and antiviral activity, but also important intermediates in organic synthesis. Therefore, the preparation of compounds containing such frameworks has attracted much attention. Common methods for constructing such frameworks include direct oxidation of disulfides or mercaptans, and sulfinate sulfide. So far, there are not many examples of preparing thiosulfonate compounds by sulfonyl hydrazine. [0003] Li et al. (Tetrahedron Letters, 58(2017), 1296-1300) developed a method for preparing thiosulfonate compounds from sulfonyl hydrazine under visible light catalysis. The rea...

Claims

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Application Information

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IPC IPC(8): C07C381/04
Inventor 张君尧魏文廷包雯慧孟亚楠孟潇潇
Owner NINGBO UNIV
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