Preparation method for thiocyanide compound

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

Active Publication Date: 2018-05-08
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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  • Preparation method for thiocyanide compound
  • Preparation method for thiocyanide compound
  • Preparation method for thiocyanide compound

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preparation example Construction

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

[0051] Mixing a mercapto compound, a thiocyanate, a catalyst and a polar organic solvent to obtain a raw material mixture, the catalyst being 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 raw material mixed liquid.

[0054]In the present invention, the simplified 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-hydroxyl-substituted phenyl, 4-nitro-substituted phenyl, 4-acetyl Substituted phenyl, halogen substituted phenyl, 3,5-bis(trifluoromethyl)-phenyl, benzyl, naphthyl, 4-meth...

Embodiment 1

[0075] Add 0.3mmol of ammonium thiocyanate, 0.1mmol of p-methylthiophenol, 1mol% rose bengal and 1mL of acetonitrile in the reaction flask, and under stirring conditions, the As a light source, the raw material mixture is illuminated, and after 12 hours of light reaction, the target product is obtained by separation and purification by column chromatography after the reaction. The column chromatography eluent used is petroleum ether and ethyl acetate with a volume ratio of 5:1 The mixed solvent, yield 85%, product purity 99.8%.

[0076] The structure of the obtained product is characterized, and the proton nuclear magnetic resonance spectrum and the carbon nuclear magnetic resonance spectrum are respectively as follows figure 1 and figure 2 As shown, the structural characterization data are 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 ): δ140.2, 131.0, 130.7, 120.6, 111.0,...

Embodiment 2

[0083] Add 0.3mmol of ammonium thiocyanate, 0.1mmol of p-methoxythiophenol, 1.2mol% rose bengal and 1mL of acetonitrile that account for the molar content of ammonium thiocyanate in the reaction flask. White light is used as the light source, and the raw material mixture is illuminated. After 11 hours of light reaction, the target product is obtained by column chromatography separation and purification after the reaction. The column chromatography eluent used is petroleum ether and acetic acid with a volume ratio of 10:1 A mixed solvent of ethyl ester, the yield is 49%, and the product purity is 99.7%.

[0084] The structure of the obtained product is characterized, and the proton nuclear magnetic resonance spectrum and the carbon nuclear magnetic resonance spectrum are respectively as follows image 3 and Figure 4 As shown, the structural characterization data are 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] 1...

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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 synthesis of organic intermediates, and in particular relates to a preparation method of thiocyanate compounds. 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 are developing 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., using 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. based on RSSR and (CH 3 ) 2 CNC-N=N-CCN(CH 3 ) 2 As a raw material, CuI is used as a catalyst to prepare thiocyanate compounds (see Zhu.D, Chang.D, Shi.L, Chem.Commun.2015, 51, 7180-7183). A...

Claims

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Application Information

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Patent Type & Authority Applications(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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