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Electrochemical preparation method of alkynyl thiocyanate

An alkynyl thiocyanate, electrochemical technology, applied in the electrolysis process, electrolysis components, electrolysis organic production and other directions, can solve the problems of complex reaction raw materials, and achieve the effects of simple and easy-to-obtain raw materials, low commercial price, and stable properties

Active Publication Date: 2019-11-15
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these methods can obtain the target products in good yields, however, most of these transformations involve the use of odorous and toxic reagents that are difficult to handle, and the reaction starting materials are complex and require the participation of transition metals

Method used

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  • Electrochemical preparation method of alkynyl thiocyanate
  • Electrochemical preparation method of alkynyl thiocyanate
  • Electrochemical preparation method of alkynyl thiocyanate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] With the platinum sheet as the anode and the platinum sheet as the cathode, add 0.2mmol phenylpropylic acid, 0.26mmol ammonium thiocyanate, 0.3mmol ammonium acetate, 0.4mmol ammonium formate, 0.1M potassium perchlorate, 6ml solvent ( Acetonitrile: water = 9:1), magnetic stirrer, turn on the power, adjust the current to 8mA, and react at room temperature for 6h. After the reaction, it was extracted three times with ethyl acetate, the organic phases were combined, dried with anhydrous magnesium sulfate, nitromethane was added as an internal standard, the yield was 82%, and the corresponding product was obtained after separation, rotary evaporation in vacuum, and purification.

[0037] The reaction of the present embodiment is shown in the following formula:

[0038]

[0039] Product NMR data:

[0040] 1 H NMR (400MHz, CDCl 3 ):δ7.51-7.49(m,2H),7.48-7.42(m,1H),7.37-7.35(m,2H)ppm.

[0041] 13 C NMR (100MHz, CDCl 3 ): δ132.4, 130.4, 128.6, 120.6, 106.4, 99.5, 62.1. ...

Embodiment 2

[0045] With the platinum sheet as the anode and the platinum sheet as the cathode, add 0.2mmol phenylpropylic acid, 0.26mmol ammonium thiocyanate, 0.3mmol ammonium acetate, 0.6mmol ammonium formate, 0.1M potassium perchlorate, 6ml solvent ( Acetonitrile: water = 9:1), magnetic stirrer, turn on the power, adjust the current to 8mA, and react at room temperature for 6h. After the reaction, it was extracted three times with ethyl acetate, the organic phases were combined, dried with anhydrous magnesium sulfate, nitromethane was added as an internal standard, the yield was 77%, and the corresponding product was obtained after separation, vacuum rotary evaporation, and purification.

[0046] The reaction of the present embodiment is shown in the following formula:

[0047]

[0048] Product NMR data:

[0049] 1 H NMR (400MHz, CDCl 3 ):δ7.51-7.49(m,2H),7.48-7.42(m,1H),7.37-7.35(m,2H)ppm.

[0050] 13 C NMR (100MHz, CDCl 3 ): δ132.4, 130.4, 128.6, 120.6, 106.4, 99.5, 62.1. of ...

Embodiment 3

[0054] With the platinum sheet as the anode and the platinum sheet as the cathode, add 0.2mmol phenylpropylic acid, 0.26mmol ammonium thiocyanate, 0.3mmol ammonium acetate, 0.2mmol ammonium formate, 0.1M potassium perchlorate, 6ml solvent ( Acetonitrile: water = 9:1), magnetic stirrer, turn on the power, adjust the current to 8mA, and react at room temperature for 6h. After the reaction, it was extracted three times with ethyl acetate, the organic phases were combined, dried with anhydrous magnesium sulfate, nitromethane was added as an internal standard, the yield was 71%, and the corresponding product was obtained after separation, rotary evaporation in vacuum, and purification.

[0055] The reaction of the present embodiment is shown in the following formula:

[0056]

[0057] Product NMR data:

[0058] 1 H NMR (400MHz, CDCl 3 ):δ7.51-7.49(m,2H),7.48-7.42(m,1H),7.37-7.35(m,2H)ppm.

[0059] 13 C NMR (100MHz, CDCl 3 ): δ132.4, 130.4, 128.6, 120.6, 106.4, 99.5, 62.1. ...

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Abstract

Belonging to the technical field of electrochemical organic synthesis, the invention discloses an electrochemical preparation method of alkynyl thiocyanate. The preparation method includes the steps of: adding a solvent (acetonitrile and water), electrolyte, alkali, a thiocyanate, phenylpropiolic acid, and negative and positive electrodes into a diaphragm-free electrolytic tank, performing stirring, and carrying out reaction under a constant current condition; and at the end of the reaction, conducting separation and purification to obtain the product alkynyl thiocyanate. The electrodes used by the method are general inert electrode, have no need for electrode modification and extra adding of various metal catalysts, thereby avoiding the use of toxic, expensive and complicatedly prepared catalyst, the reaction yield is high, the reaction system is simple, and the operation is carried out under normal temperature and pressure, the method is simple and safe, and is suitable for large-scale industrial production.

Description

technical field [0001] The invention belongs to the technical field of electrochemical organic synthesis, and in particular relates to an electrochemical preparation method of alkynyl thiocyanate. Background technique [0002] Organic sulfur-containing compounds widely exist in our daily life. They not only exist in our body as cysteine ​​and methionine, but also are the main components of penicillin, nelfinavir and quetiapine and other drugs. As an important part of organic sulfides, alkynyl thiocyanate compounds can not only be oxidized into α-thiocyanoketone, but also use it as a functional molecule to generate four thiocyanate compounds under the action of azide, aniline, and sodium borohydride, respectively. oxazole, aminothiazole and thiazolidine and other key drug intermediates, and can also be decyanated and trifluoromethylated to synthesize alkynyl trifluoromethyl sulfide and alkynyl sulfide compounds under the action of trifluoro reagent and Grignard reagent. Expa...

Claims

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Application Information

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IPC IPC(8): C25B3/00
CPCC25B3/00
Inventor 黄精美杨顺铭
Owner SOUTH CHINA UNIV OF TECH
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