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Preparation method of s-triazine compound

A compound, the technology of s-triazine, which is applied in the field of preparation of s-triazine compounds, achieves the effects of low cost, wide industrial application prospect and convenient operation

Active Publication Date: 2016-07-13
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Among them, s-triazine compounds are a relatively common class of triazine compounds. The preparation of such compounds is mainly through the reaction of cyanoguanidine and nitrile compounds, the reaction of biguanide and ester compounds, the reaction of amides and dimethyl acetal And amidine or guanidine reaction, etc., but these synthetic methods have certain limitations

Method used

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  • Preparation method of s-triazine compound
  • Preparation method of s-triazine compound
  • Preparation method of s-triazine compound

Examples

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Embodiment 1

[0018] The present invention will be further described below through specific examples, but the protection scope of the present invention is not limited thereto. Embodiment 1: the preparation of compound (III-1)

[0019] In a reaction vessel, add metformin hydrochloride (0.1653g, 0.9954mmol), benzyl alcohol (0.1082g, 1.0002mmol), 1,5-cyclooctadiene ruthenium dichloride (0.0056g, 0.02mmol), tert-butyl Potassium alcoholate (0.2250g, 2.0052mmol), 1,4-dioxane (4mL), stirred and reacted in an oil bath at 100°C for 15 hours; after the reaction, add water (10mL), extract with ethyl acetate (10mL× 3), the organic layers were combined, dried with anhydrous sodium sulfate, filtered, and the filtrate was concentrated, and the obtained concentrate was separated by column chromatography, and the eluent was dichloromethane:methanol=50:1 (V:V), and R f The eluate with a value of 0.3-0.35 (monitored by TLC, the developing solvent is the same as the eluent) was distilled under reduced pressur...

Embodiment 2

[0023] Change 1,5-cyclooctadiene ruthenium dichloride to dodecacarbonyl ruthenium (0.0128g, 0.02mmol), other operations are the same as in Example 1, and finally obtain the target compound (III-1) 0.1586g, the yield is 74 %.

Embodiment 3

[0025] 1,5-Cyclooctadiene ruthenium dichloride was changed to triphenylphosphine ruthenium chloride (0.0182g, 0.02mmol), and other operations were the same as in Example 1 to finally obtain 0.1180g of the target compound (III-1). The rate is 55%.

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Abstract

The invention provides a preparation method of an s-triazine compound shown in formula (III). The preparation method comprises steps as follows: an alcohol compound shown in formula (I), biguanide hydrochloride shown in formula (II), a metal ruthenium catalyst and an alkaline matter are added to a solvent and subjected to a stirring reaction at 80-130 DEG C for 10-18 h, and then the s-triazine compound shown in formula (III) is obtained after post-treatment of a reaction liquid. The preparation method is convenient to operate and low in cost and has wide industrial application prospect, the reaction condition is mild, and raw materials are easy to obtain.

Description

(1) Technical field [0001] The invention relates to a preparation method of s-triazine compounds. (2) Background technology [0002] Triazine compounds have various biological activities such as anticancer, antibacterial, antimalarial, and herbicide, and are widely used in medicine, pesticides and other fields. Among them, s-triazine compounds are a relatively common class of triazine compounds. The preparation of such compounds is mainly through the reaction of cyanoguanidine and nitrile compounds, the reaction of biguanide and ester compounds, the reaction of amides and dimethyl acetal And amidine or guanidine reaction, etc., but these synthetic methods have certain limitations. Therefore, it is of great theoretical significance and practical application value to study the preparation method of s-triazine compounds. (3) Contents of the invention [0003] The purpose of this invention is to provide a kind of preparation method of s-triazine compound. [0004] The prese...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D251/48C07D409/04C07D405/04
CPCC07D251/48C07D405/04C07D409/04
Inventor 崔冬梅曾明吴空张辰
Owner ZHEJIANG UNIV OF TECH
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