Preparation method of benzyl isothiocyanate compound

A technology of benzyl isothiocyanate and compound, applied in the field of preparation of benzyl isothiocyanate compounds, can solve problems such as complicated steps, severe reaction conditions, etc., and achieves simple operation, easily available raw materials, and mild reaction conditions. Effect

Inactive Publication Date: 2022-01-04
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Utilize above-mentioned method to synthesize benzyl isothiocyanate compound, have obvious shortcoming and deficiency: 1) step is loaded down with trivial details; 2) use poisonous reagent; 3) reaction condition is severe

Method used

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  • Preparation method of benzyl isothiocyanate compound
  • Preparation method of benzyl isothiocyanate compound
  • Preparation method of benzyl isothiocyanate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Preparation of benzyl isothiocyanate compound 3a

[0022]

[0023] Add 4-ethylanisole 1a (0.3mmol, 41mg), trimethylsilyl isothiocyanate 2 (0.6mmol, 79mg), tetrabutyl ammonium hexafluorophosphonate (0.6mmol, 232mg) and dichloroethane and hexafluoroisopropanol (3:1, 6mL). Graphite felt (1cm x 1.5cm x 1cm) was used as the anode and a nickel sheet (1cm x 1cm x 0.1mm) was used as the cathode. The reaction mixture was stirred at room temperature for 6 hours at a constant current of 7 mA. After the reaction was complete, the solvent was removed using a rotary evaporator. The product 3a was obtained by silica gel column chromatography using petroleum ether and ethyl acetate (20:1) as eluent with a yield of 72%.

[0024] Spectral analysis data 3a:

[0025] 1 H NMR (500MHz, CDCl 3 )δ7.25(d, J=8.5Hz, 2H), 6.90(d, J=8.7Hz, 2H), 4.87(q, J=6.8Hz, 1H), 3.81(s, 3H), 1.65(d, J=6.8Hz,3H).

[0026] 13 C NMR (125MHz, CDCl 3 )δ159.6, 132.4, 132.1, 126.9, 114.3, 56.7, 55.5, 25.0...

Embodiment 2

[0028]

[0029] Add p-bromoethylbenzene 1b (0.3mmol, 56mg), trimethylsilyl isothiocyanate 2 (0.6mmol, 79mg), tetrabutylammonium perchlorate (0.6mmol, 205mg) and di Ethyl chloride and hexafluoroisopropanol (3:1, 6mL). Graphite felt (1cm x 1.5cm x 1cm) was used as the anode and a nickel sheet (1cm x 1cm x 0.1mm) was used as the cathode. The reaction mixture was stirred at room temperature for 6 hours at a constant current of 7 mA. After the reaction was complete, the solvent was removed using a rotary evaporator. The product 3b was obtained by silica gel column chromatography using petroleum ether and ethyl acetate (40:1) as eluent with a yield of 62%.

[0030] Spectrum analysis data 3b:

[0031] 1 H NMR (500MHz, CDCl 3 )δ7.51(d, J=8.5Hz, 2H), 7.20(d, J=8.5Hz, 2H), 4.88(q, J=6.8Hz, 1H), 1.65(d, J=6.8Hz, 3H) .

[0032] 13 C NMR (125MHz, CDCl 3 )δ139.3, 133.5, 132.2, 127.3, 122.2, 56.6, 25.0.

Embodiment 3

[0034] Replace 1b in Example 2 with 1c, and other conditions are the same as Example 2. The experimental results are shown in Table 1.

[0035]

[0036] Spectrum analysis data 3c:

[0037] 1 H NMR (500MHz, CDCl 3 )δ7.35(d, J=8.4Hz, 2H), 7.26(d, J=8.5Hz, 2H), 4.90(q, J=6.8Hz, 1H), 1.65(d, J=6.8Hz, 3H) .

[0038] 13 C NMR (125MHz, CDCl 3 )δ138.8, 134.2, 133.4, 129.2, 127.0, 56.6, 25.1.

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Abstract

The invention discloses a preparation method of a benzyl isothiocyanate compound, and belongs to the technical field of organic synthesis. The method comprises the following steps: adding benzyl benzene, trimethylsilyl isothiocyanate, an electrolyte and a solvent into a reactor, reacting under the action of constant current, and after the reaction is finished, separating by silica gel column chromatography to obtain the pure target product. The preparation method of the benzyl isothiocyanate compound provided by the invention has the characteristics of being scientific and reasonable, mild in condition, simple to operate and the like. The reaction equation is shown in the specification.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of benzyl isothiocyanate compounds. Background technique [0002] Benzyl isothiocyanate compounds widely exist in natural products and drug molecules, and are also important synthetic intermediates for the synthesis of thiourea or heterocyclic derivatives. Studies have shown that these compounds have various biological activities, such as bactericidal (Molecules 2018, 23, 624), anti-cancer (Cancer Res. 2015, 75, 5130), etc. It has important application value in the fields of medicine and pesticide. Therefore, it is of great significance to develop a new method for the green and efficient synthesis of benzyl isothiocyanate compounds. [0003] The preparation method of benzyl isothiocyanate compound has: [0004] 1) Using amine and carbon disulfide as raw materials [0005] Dolman's research group prepared benzyl isothiocyanate compoun...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C25B3/09C25B3/11C25B3/07C25B3/20
CPCC25B3/09C25B3/11C25B3/07C25B3/20
Inventor 文丽荣张善学郭维斯李明
Owner QINGDAO UNIV OF SCI & TECH
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