Preparation method of 5-amino-6-methyl benzimidazolone

A technology of methylbenzimidazolone and diaminotoluene, which is applied in the field of compound preparation, can solve the problems of unreported reduction yield, unreported product quality, and unexplained catalyst manufacture, etc., and achieves low production cost, catalytic Good effect and low cost effect

Active Publication Date: 2010-10-20
淄博圣马化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the patent does not report the quality of the obtained product, and the catalyst used for hydrogenation reduction in this process is self-made, and the patent does not clearly explain the manufacture of the catalyst
The third document is a patent applied by Cotico Co., Ltd. of Australia in China. The patent publication number is CN1675185. This patent adopts the three-step unit operation route of rin

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] In a 2000ml four-neck flask equipped with stirring, reflux condenser, thermometer, and heating electric heating mantle, add 1400g of o-dichlorobenzene, then start stirring, and add 244g (2.0mol) 3,4-dichlorobenzene under stirring conditions. After adding aminotoluene and 123g (2.05mol) urea, turn on the heating mantle heating system, slowly raise the temperature of the system to 143°C within 1.0 hour, and keep the reaction at 143-147°C for 5.5 hours. , remove the electric heating mantle, and cool down naturally under stirring. When the temperature is lower than 100°C, continue to lower the system temperature to within 30°C with a water bath, filter, wash with water, and then dry under an infrared lamp to obtain 5-methylbenzo Imidazolone 293.6g, purity 99.3%, yield 98.5%.

[0016] With a 1000ml clean four-necked bottle, install stirring, a thermometer, an addition funnel, and a constant temperature water bath, then add 814g of 30% nitric acid (3.876mol) to it, start stir...

Embodiment 2

[0019] In a 2000ml four-neck flask equipped with stirring, reflux condenser, thermometer, and heating electric heating mantle, add 1400g of o-dichlorobenzene, then start stirring, and add 244g (2.0mol) 3,4-dichlorobenzene under stirring conditions. After adding aminotoluene and 123g (2.05mol) urea, turn on the heating mantle heating system, slowly raise the temperature of the system to 182°C within 1.0 hour, and keep the reaction at 182-185°C for 5.5 hours. , remove the electric heating mantle, and cool down naturally under stirring. When the temperature is lower than 100°C, continue to lower the system temperature to within 30°C with a water bath, filter, wash with water, and then dry under an infrared lamp to obtain 5-methylbenzo Imidazolone 287.9g, purity 98.5%, yield 95.8%.

[0020] The product obtained above was reacted according to the nitration process in Example 1 to obtain 133.8 g of 5-nitro-6-methylbenzimidazolone with a purity of 99.2% and a yield of 98.2%.

[0021...

Embodiment 3

[0023] In a 2000ml four-neck flask equipped with stirring, reflux condenser, thermometer, and heating electric heating mantle, add 1400g of o-dichlorobenzene, then start stirring, and add 244g (2.0mol) 3,4-dichlorobenzene under stirring conditions. After adding aminotoluene and 123g (2.05mol) urea, turn on the heating mantle heating system, slowly raise the temperature of the system to 131°C within 1.0 hour, and keep it at 130-134°C for 7.5 hours. , remove the electric heating mantle, and cool down naturally under stirring. When the temperature is lower than 100°C, continue to lower the system temperature to within 30°C with a water bath, filter, wash with water, and then dry under an infrared lamp to obtain 5-methylbenzo Imidazolone 273.4g, purity 98.3%, yield 90.8%.

[0024] The product obtained above was reacted according to the nitration process in Example 1 to obtain 133.1 g of 5-nitro-6-methylbenzimidazolone with a purity of 99.3% and a yield of 97.8%.

[0025]Install a...

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PUM

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Abstract

The invention relates to a preparation method of 5-amino-6-methyl benzimidazolone, belonging to the technical field of a compound preparation method, in particular to a preparation method of fine chemical intermediate. The preparation method is characterized by sequentially comprising the following steps of: carrying out condensation on 3, 4-diaminotoluene and urea, and preparing 5-methyl benzimidazolone; carrying out nitration reaction on the 5-methyl benzimidazolone under the condition of dilute nitric acid, and preparing 5-nitro-6-methyl benzimidazolone; and finally, carrying out reduction reaction on the 5-nitro-6-methyl benzimidazolone, and preparing the target compound of 5-amino-6-methyl benzimidazolone. In the reduction process of ferrous powder of the reduction reaction of the preparation method, alcohol-water system is taken as a solvent, and the system has low toxicity. In the process of hydrogenation reduction process, DMF-water system is taken as a solvent, and the solvent can be easily recovered, so that the cost is saved. In the process of hydrogenation reduction process, Nguyen Ni or Pd carbon is taken as a catalyst, so that the catalysis effect is good, the cost is low, and the synthetic route has simple technique.

Description

technical field [0001] The invention belongs to the technical field of compound preparation methods, and in particular relates to a preparation method of a fine chemical intermediate. Background technique [0002] 5-Amino-6-methylbenzimidazolone is a valuable fine chemical intermediate, which is not only used in the synthesis of various organic pigments, but also in the fields of dyes and medicines. Since the late 1980s, many companies such as Dominion Company in Canada, Klein Company in Germany, and Chibagaki Company in Switzerland have done in-depth and extensive research on the application field of this product, and have also made great achievements. With the development of the industry, many deep-processed products with excellent application performance have been obtained. But so far, there are few reports on the synthesis of 5-amino-6-methylbenzimidazolone. In our search of related documents including CA and Beil., we only found three articles about 5-amino-6 Reports ...

Claims

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Application Information

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IPC IPC(8): C07D235/26
Inventor 谭立哲于先进张小华
Owner 淄博圣马化工有限公司
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