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Imidazole-2-thioketone compound preparation method

An ester compound and compound technology are applied in the field of preparation of imidazole-2-thione compounds and can solve problems such as complicated operation

Active Publication Date: 2018-09-28
GANNAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the above reaction route can successfully prepare imidazole-2-thione compounds, the reaction process requires multiple steps, and each step requires separation and purification after the reaction, which makes the operation complicated

Method used

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preparation example Construction

[0043] The invention provides a kind of preparation method of imidazole-2-thiones compound, comprises the following steps:

[0044] mixing amidine compounds, isothiocyanate compounds, α-halogenated ketone compounds and an organic solvent to obtain a raw material mixture;

[0045] adjusting the pH value of the raw material mixture to alkaline to obtain an alkaline reaction solution;

[0046] The alkaline reaction solution undergoes a series cyclization reaction under heating conditions to obtain imidazole-2-thione compounds.

[0047] The invention mixes amidine compounds, isothiocyanate compounds, alpha-halogenated ketone compounds and organic solvents to obtain a raw material mixture. In the present invention, the structural formula of the amidine compound is preferably R 2 NH=CNH 2 , the R 2 Preferred are phenyl, alkyl-substituted phenyl, alkoxy-substituted phenyl, trifluoromethyl-substituted phenyl, halogen-substituted phenyl, cycloalkyl, alkyl or amine groups. In the p...

Embodiment 1

[0068] Mix 0.1mmol benzamidine, 0.1mmol phenyl isothiocyanate, 0.3mmol ethyl 2-bromoacetate, 0.3mmol sodium hydroxide and 1mL acetonitrile, heat at 70°C, stir for 12h to carry out a series cyclization reaction; After the series cyclization reaction is finished, the resulting material is subjected to column chromatography purification treatment (the eluent used is a mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 5:1), and the gained eluent is spin-dried to obtain the product, The yield was 52% and the purity was 99.9%.

[0069] 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:

[0070] 1 H NMR (400MHz, DMSO): δ=10.79(s, 1H), δ=7.74-7.72(m, 2H), δ=7.64-7.62(d, J=8Hz, 2H), δ=7.44-7.43(t ,J=4Hz,3H),δ=7.39-7.35(t,J=16Hz,2H),δ=7.07-7....

Embodiment 2

[0076] Mix 0.1mmol p-trifluoromethyl benzamidine, 0.1mmol phenyl isothiocyanate, 0.3mmol ethyl 2-bromoacetate, 0.3mmol sodium hydroxide and 1mL acetonitrile, heat at 70°C, stir for 12h to carry out series ring reaction; after the completion of the series cyclization reaction, the gained material is subjected to column chromatography purification treatment (the eluent used is a mixed solvent of sherwood oil and ethyl acetate with a volume ratio of 5:1), and the gained eluent is vortexed Drying yielded the product in 59% yield and 99.8% purity.

[0077] 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:

[0078] 1 H NMR (400MHz, CDCl 3 ): δ=9.26(s, 1H), δ=7.78-7.76(d, J=8Hz, 2H), δ=7.53-7.51(d, J=8Hz, 2H), δ=7.269-7.25(m, 2H ),δ=7.15-7.11(m,1H),δ=7.09-7.07(...

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Abstract

The invention provides an imidazole-2-thioketone compound preparation method. According to the method, an amidine compound, an isorhodanate compound, an alpha-halogenated ketone compound, and an organic solvent are mixed to obtain raw material mixed liquor; a pH value of the raw material mixed liquor is adjusted to alkalescence, and an alkalescence reaction solution is obtained; and a series cyclisation reaction of the alkalescence reaction solution is generated under heating condition to obtain the imidazole-2-thioketone compound. During the invention, heating provides the required energy forthe series cyclisation reaction, selection of the raw materials can be cooperated, under alkaline condition, through C-N bond rupture, a target product of an imidazole-2-thioketone compound is obtained, the reaction step is less, the operation is simple, control is easy, and a metal catalyst is not required; adaptability on the raw materials is strong, and the purity of the imidazole-2-thioketonecompound is high, which can achieve 98.5-99.9%, so that the method has the large market popularization value.

Description

technical field [0001] The invention relates to the technical field of organic intermediate synthesis, in particular to a preparation method of imidazole-2-thione compounds. Background technique [0002] Imidazole widely exists in various natural products and has good biological activity. Among them, imidazole-2-thione is the basic structural unit of many natural products, bioactive molecules and drug molecules. Compounds with imidazole-2-thione structural units have various physiological activities, such as antibacterial activity, antitumor activity and anticytokine activity, and can be used to prepare receptor inhibitors to inhibit c-Jun N-terminal kinase 3 and p38α mitogenicity Proactivated protein kinase is used in the treatment of Huntington's disease, etc.; in addition, some imidazole-2-thione derivatives are used as organic catalysts to promote enantioselective Friedel-Crafts alkylation. Based on this, imidazole-2-thione compounds have attracted widespread attention....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/90
CPCC07D233/90
Inventor 郭维赵明明郑绿茵谭文范小林
Owner GANNAN NORMAL UNIV
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