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Method for synthesis of high purity trimethyl silicon based imidazole

A technology of trimethylsilyl imidazole and a synthesis method, which is applied in the directions of silicon organic compounds, sustainable manufacturing/processing, climate sustainability, etc. It can reduce the production of imidazole and silyl ether, shorten the reaction time, and simplify the process flow.

Active Publication Date: 2009-02-18
ZHEJIANG UNIV +1
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  • Summary
  • Abstract
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AI Technical Summary

Problems solved by technology

The trimethylsilyl chloride method is a traditional method for synthesizing trimethylsilyl imidazole. This method reacts with imidazole and trimethylchlorosilane. Since hydrogen chloride will be generated in the reaction, a large amount of triethylamine must be added in the reaction as hydrogen chloride receptors, the selectivity of the reaction is not high
Because trimethylsilyl imidazole has poor thermal stability and is easy to react with water to generate imidazole and hexamethyldisiloxane, therefore, in various methods for synthesizing trimethylsilyl imidazole, low reaction yields generally exist , poor selectivity, easy decomposition of products, and large environmental pollution. It is necessary to seek a method for synthesizing trimethylsilyl imidazole with high reaction yield, good selectivity, high product purity, and less environmental pollution.

Method used

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  • Method for synthesis of high purity trimethyl silicon based imidazole
  • Method for synthesis of high purity trimethyl silicon based imidazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Add 34g (0.5mol) imidazole and 1.2g (0.002mol) magnesium stearate in a 250 milliliter three-necked flask with constant pressure dropping funnel, thermometer, magnetic stirring and 1 meter rectifying column, and 96.6g (0.6 mol) hexamethyldisilazane was added to the constant pressure dropping funnel. Then heat, turn on magnetic stirring, control the temperature of the reaction kettle at about 140°C, slowly add hexamethyldisilazane dropwise from the constant pressure funnel, and rectify while reacting, the produced by-product ammonia gas is absorbed by water, and the rectification column The fraction below 105°C was collected at the top, and the reaction time was controlled to be 2 hours. After the reaction, the reaction solution was rectified under reduced pressure to obtain a high-content trimethylsilyl imidazole product with a yield of 88% and a content of 99.3%.

Embodiment 3-8

[0018] Similar to Example 1, the control reaction temperature is 140 DEG C, and the reaction time is 2 hours, and the type of stabilizer and the amount of catalyst are changed, and the reaction results are as follows (Table 1):

[0019] Table 1 Effects of different stabilizer types and amounts on the reaction

[0020]

Embodiment 9-15

[0022] Similar to Example 1, using zinc stearate as a stabilizer, the molar ratio of zinc stearate and imidazole is 0.001: 1, the molar ratio of hexamethyldisilazane and imidazole is 1.2: 1, change the reaction temperature, The condition of reaction pressure and reaction time, reaction result is as follows table (table two):

[0023] Table 2 The influence of different reaction conditions on the reaction

[0024]

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Abstract

The present invention relates to a novel method for synthesizing high-purity N-trimethylsilylimidazole, which uses hexamethyldisilazane and imidazole as materials and adopts the reactive distillation technology to synthesize the high-purity N-trimethylsilylimidazole under the existence of phosphite ester stabilizer. The molar ratio of the hexamethyldisilazane and the imidazole is 10:1 to 1:2; the molar ratio of the stabilizer and the imidazole is 0.0001:1 to 0.05:1; and under the reaction temperature of 100 DEG C to 200 DEG C, reaction lasts for 1-16 hours until the high-purity N-trimethylsilylimidazole is prepared. The method has the advantages of high reaction conversion rate, good selectivity, high product quality, low energy consumption, little environment pollution, and the like.

Description

technical field [0001] The invention relates to a method for synthesizing high-purity trimethylsilyl imidazole by reactive distillation technology using hexamethyldisilazane and imidazole as raw materials in the presence of a stabilizer. Background technique [0002] Trimethylsilyl imidazole is an important basic silylating protection reagent and a key raw material for the synthesis of important neutral silylating reagent bis(trimethylsilyl)acetamide, which is used in amino acids, carboxylic acids, alcohols and amides It is widely used in the silanization protection, especially in the synthesis of cephalosporin antibiotics. Cephalosporin antibiotics are a class of antibiotics with the fastest development, the most varieties and the fastest speed in foreign countries since the 1970s. Because of its wide antibacterial spectrum, strong bactericidal power, high stability to β-lactamase, lower toxic and side effects than semi-synthetic penicillins, and good clinical efficacy, it...

Claims

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Application Information

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IPC IPC(8): C07F7/08
CPCY02P20/10
Inventor 王从敏胡文江吴建平陈思先
Owner ZHEJIANG UNIV
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