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A kind of preparation method of thiocyanate compound

A technology of ester compounds and thiocyanate, applied in organic chemistry methods, chemical instruments and methods, organic chemistry, etc., can solve problems such as heavy metal residues in thiocyanate compounds, affecting the application of thiocyanate compounds, etc. Achieve the effect of avoiding adverse effects and easy removal

Active Publication Date: 2020-07-31
GANNAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the above method can prepare thiocyanate compounds, heavy metal catalysts such as CuCl or CuI need to be used in the preparation process. Even after subsequent purification treatment, there are still heavy metal residues in the obtained thiocyanate compounds, which affects Application of Thiocyanate Compounds

Method used

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  • A kind of preparation method of thiocyanate compound
  • A kind of preparation method of thiocyanate compound
  • A kind of preparation method of thiocyanate compound

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preparation example Construction

[0050] The invention provides a preparation method of a thiocyanate compound, including:

[0051] Mixing a mercapto compound, thiocyanate, a catalyst and a polar organic solvent to obtain a raw material mixture, wherein the catalyst is rose bengal, eosin Y or eosin B;

[0052] The raw material mixture is subjected to light reaction under light conditions to obtain thiocyanate compounds.

[0053] The invention mixes mercapto compound, thiocyanate, catalyst and polar organic solvent to obtain a raw material mixture.

[0054] In the present invention, the structural formula of the mercapto compound is R-SH, and the R is preferably an aryl group, a benzyl group or an azacyclic group. The aryl group is preferably alkyl-substituted phenyl, alkoxy-substituted phenyl, 4-amino-substituted phenyl, 4-hydroxy-substituted phenyl, 4-nitro-substituted phenyl, 4-acetyl Substituted phenyl, halogen substituted phenyl, 3,5-bis(trifluoromethyl)-phenyl, benzyl, naphthyl, 4-methoxybenzyl, 4-chlorobenzyl; ...

Embodiment 1

[0075] Add 0.3mmol of ammonium thiocyanate, 0.1mmol of p-methyl thiophenol, rose bengal with a molar content of 1 mol% of ammonium thiocyanate, and 1 mL of acetonitrile into the reaction flask. Under stirring conditions, use 6000k white light As a light source, the raw material mixture is illuminated. After 12 hours of light reaction, the target product is separated and purified by column chromatography after the reaction is completed. The column chromatography eluent used is petroleum ether and ethyl acetate in a volume ratio of 5:1 The mixed solvent, the yield is 85%, and the product purity is 99.8%.

[0076] Characterize the structure of the obtained product, the proton nuclear magnetic resonance spectrum and the carbon nuclear magnetic resonance spectrum are as follows: figure 1 with figure 2 As shown, the structural characterization data is as follows:

[0077] 1 H NMR(400MHz, CDCl 3 ): δ7.43(d,J=8.0Hz,2H), 7.24(d,J=8.0Hz,2H), 2.38(s,3H)ppm.

[0078] 13 C NMR(100MHz, CDCl 3 ):...

Embodiment 2

[0083] Add 0.3mmol of ammonium thiocyanate, 0.1mmol of p-methoxy thiophenol, 1.2 mol% of rose bengal, and 1 mL of acetonitrile into the reaction flask. The white light is the light source, and the raw material mixture is illuminated. After 11 hours of light reaction, after the reaction, the target product is separated and purified by column chromatography. The column chromatography eluent used is 10:1 petroleum ether and acetic acid in volume ratio The mixed solvent of ethyl ester has a yield of 49% and a product purity of 99.7%.

[0084] Characterize the structure of the obtained product, the proton nuclear magnetic resonance spectrum and the carbon nuclear magnetic resonance spectrum are as follows: image 3 with Figure 4 As shown, the structural characterization data is as follows:

[0085] 1 H NMR(400MHz, CDCl 3 ): δ7.51-7.49 (m, 2H), 6.96-6.94 (m, 2H), 3.83 (s, 3H) ppm;

[0086] 13 C NMR(100MHz, CDCl 3 ): δ161.3, 133.8, 115.9, 113.8, 111.6, 55.6ppm.

[0087] MS (EI, 70eV): m / z ...

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Abstract

The invention discloses a preparation method for a thiocyanide compound. The preparation method comprises the following steps: taking a sulfhydryl compound, thiocyanate as raw materials, taking rose-bengal, eosine Y or eosin B as a catalyst, performing illumination, generating a thiocyanide compound after the illumination reaction. According to the preparation method provided by the invention, thiocyanide is decomposed into thiocyanate ions; the sulfhydryl compound generates sulfhydryl radical under the action of light and the catalyst, and the sulfhydryl radical is used for attacking carbon atoms in thiocyanate ions to obtain a intermediate; sulfide is removed from the intermediate to obtain the thiocyanide compound. The rose-bengal, the eosine Y or the eosin B used by the method containno heavy metal ion, and the adverse effect on the performance of the thiocyanide compound by the heavy metal ion residue is avoided; in addition, the catalyst is easily removed, so that a favorable condition is provided for the preparation of the thiocyanide compound with higher purity.

Description

Technical field [0001] The invention belongs to the field of organic intermediate synthesis, and specifically relates to a preparation method of a thiocyanate compound. Background technique [0002] Thiocyanate compounds are important organic intermediates and can be widely used in the synthesis of biologically active organic compounds. Therefore, the preparation methods of thiocyanate compounds have been developed more and more rapidly. At present, thiocyanate compounds are mostly prepared under the action of heavy metal catalysts, such as Sun.N, Che.L, etc. with trimethylsilyl isocyanate (TMSNCS) and ph-B(OH) 2 As a raw material, CuCl is a catalyst to prepare thiocyanate compounds (see Sun.N, Che.L, Mo.W, Hu.B, Shen.Z, Hu.X, Org.Biomol.Chem.2015,13,691- 696); Zhu.D, Chang.D, etc. use RSSR and (CH 3 ) 2 CNC-N=N-CCN(CH 3 ) 2 As a raw material, CuI is a catalyst to prepare thiocyanate compounds (see Zhu. D, Chang. D, Shi. L, Chem. Commun. 2015, 51, 7180-7183). Although the above ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B45/00C07C331/04C07C331/08C07C331/10C07C331/12C07D277/74C07D285/125
CPCC07B45/00C07C331/04C07C331/08C07C331/10C07C331/12C07D277/74C07D285/125
Inventor 郭维谭雯赵明明郑绿茵陈德良范小林
Owner GANNAN NORMAL UNIV
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