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Chemical synthesis method of pyrimidine thioketone

A technology for the chemical synthesis of pyridinethione, which is applied in the field of chemical synthesis of pyridinethione, can solve the problems of low product yield and purity, large amount of catalyst, troublesome post-processing, etc., and achieve low production cost, no three wastes, and clean reaction. high rate effect

Inactive Publication Date: 2006-07-19
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At the same time, during the reaction process, the concentrated hydrochloric acid is also very corrosive to the equipment.
[0003] As a catalyst, the traditional Lewis acid can improve the reaction efficiency under certain conditions, and has been widely used in organic synthesis. However, the disadvantage of these production processes is that the amount of catalyst is large, because most of the traditional Lewis acids are decomposed by water and become invalid. It must be strictly controlled under anhydrous conditions, and for nitrogen-containing or imine compounds, nitrogen atoms will inhibit the catalytic activity of Lewis acids, and a large amount is required to meet the reaction. Disadvantages such as low yield and purity

Method used

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  • Chemical synthesis method of pyrimidine thioketone
  • Chemical synthesis method of pyrimidine thioketone
  • Chemical synthesis method of pyrimidine thioketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The molar ratio of the feed material is aldehyde (II): β-diketone or β-ketoester (III): substituted thiourea (IV): magnesium trifluoromethanesulfonate is 1: 1.0: 1.5: 0.15, and the aldehyde is benzene Formaldehyde, β-diketone or β-ketoester is ethyl acetoacetate, thiourea is substituted for thiourea, and ethanol is used as an organic solvent, the amount of which is 10 times the mass of benzaldehyde.

[0028] In a 250mL four-neck flask equipped with a thermometer, a reflux condenser and a mechanical stirrer, add 50mmol of benzaldehyde, 75mmol of thiourea, 50mmol of ethyl acetoacetate and 7.5mmol of magnesium trifluoromethanesulfonate (2.40g), and use 53g of ethanol to Dissolve, stir well at room temperature until completely dissolved. Raise the temperature to 70°C for reaction, follow and monitor with HPLC during the reaction (flow rate: 1.0mL / min, methanol: water = 60:40), after 4 hours the reaction is complete to obtain the reaction product, cool to room temperature, f...

Embodiment 2

[0032] The molar ratio of the feed material is aldehyde (II): β-diketone or β-ketoester (III): substituted thiourea (IV): magnesium trifluoromethanesulfonate=1: 1.0: 1.5: 0.15, and the aldehyde is benzene Formaldehyde, β-diketone or β-ketoester is ethyl acetoacetate, thiourea is substituted for thiourea, acetonitrile is used as an organic solvent, and its consumption is 10 times the mass of benzaldehyde. The reaction temperature was 70°C, and the reaction time was 6 hours.

[0033] Other operations are the same as in Example 1, the product yield is 93.0%, the purity is 99.1%, the melting point is 207.1-208.0°C, and the recovery rate of magnesium trifluoromethanesulfonate is 95%.

Embodiment 3

[0035] The ratio of the amount of feed material to aldehyde (II): β-diketone or β-ketoester (III): substituted thiourea (IV): magnesium trifluoromethanesulfonate=1: 1.0: 1.5: 0.15, and aldehyde is benzaldehyde , β-diketone or β-ketoester is ethyl acetoacetate, thiourea is substituted for thiourea, ethyl acetate is used as an organic solvent, and its consumption is 10 times the mass of benzaldehyde. The reaction temperature is the reflux temperature of ethyl acetate, and the reaction time is 6 hours.

[0036]Other operations are the same as in Example 1, the product yield is 91.2%, the purity is 98.6%, the melting point is 207.0-208.5°C, and the recovery rate of magnesium trifluoromethanesulfonate is 94%.

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Abstract

The related synthesis method for pyrimidinethione compound comprises: using trifluoro magnesium methanesulfonate to replace traditional Lewis acid catalyst of strong HCl and ZnCl2, selecting aldehyde and beta-diketone instead of thiourea as material to reaction at 20-150Deg. This invention has yield and purity more than 85% and 98.5% respectively with low cost and mild condition, and produces almost no three wastes.

Description

(1) Technical field [0001] The present invention relates to a kind of chemical synthesis method of pyrimidinethione, in particular to the use of magnesium trifluoromethanesulfonate [Mg(OTf) 2 ] instead of concentrated hydrochloric acid, zinc dichloride, BF 3 ·OEt 2 The traditional Lewis acid to prepare pyrimidinethione chemical synthesis method. (2) Background technology [0002] Before the present invention provides, the chemical synthesis method of pyrimidinethione in the prior art is based on concentrated hydrochloric acid, zinc dichloride, BF 3 ·OEt 2 Such as the traditional Lewis acid as a catalyst to prepare. If concentrated hydrochloric acid is used as a catalyst, the reaction temperature is high, the time is 18 hours, and the yield is about 20-50%. At the same time, during the reaction process, the concentrated hydrochloric acid is also highly corrosive to the equipment. [0003] As a catalyst, the traditional Lewis acid can improve the reaction efficiency unde...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/22
Inventor 苏为科李坚军
Owner ZHEJIANG UNIV OF TECH
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