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Preparation method of 2-(3-amino phenyl) imidazoline hydrochloride and imidocarb

A kind of technology of imidazoline hydrochloride, aminophenyl, applied in chemical field

Inactive Publication Date: 2017-07-18
GUANNAN YISITE CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] Purpose of the invention: Aiming at the problems of pollution or safety risks in the prior art, the present invention provides a method for preparing 2-(3-aminophenyl)imidazoline hydrochloride and imidazolium, which uses transfer hydrogenation to prepare 2 -(3-aminophenyl) imidazoline aqueous solution, and use the prepared 2-(3-aminophenyl) imidazoline aqueous solution to prepare 2-(3-aminophenyl) imidazoline hydrochloride, and then prepare imidazoline Urea; no pollution in the preparation process, no safety risk

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach 1

[0028] 1. Preparation of 2-(3-nitrophenyl) imidazoline:

[0029] In a 200L reactor with a reflux device, add 100L of methanol, 14.8kg of m-nitrobenzonitrile, 1.6kg of sulfur and 8L of ethylenediamine under stirring; heat up slowly, and keep the temperature at about After reacting at around 67°C for 24 hours, take samples for testing. After the ring closure reaction between m-nitrobenzonitrile and ethylenediamine fully occurs under the catalysis of sulfur, the residue of m-nitrobenzonitrile should be controlled below 2%. Properly add ethylenediamine to continue the reaction (approximately 2L of ethylenediamine is added, and the reaction is continued for about 8-10h); after the reaction is completed, most of the methanol is evaporated, and the temperature is lowered to 0°C to precipitate 2-(3-nitrophenyl ) imidazoline solid, suction filtration, the filtrate continued to concentrate and crystallize 2-(3-nitrophenyl) imidazoline, suction filtration; combined the aforementioned 2-(...

Embodiment approach 2

[0037] 1. Preparation of 2-(3-nitrophenyl)imidazoline: the preparation method is the same as in Embodiment 1.

[0038] Two, prepare 2-(3-aminophenyl) imidazoline hydrochloride:

[0039] Put 6kg of 2-(3-nitrophenyl)imidazoline, 0.6kg of palladium carbon and 60L of methanol aqueous solution into a 100L enamel reaction kettle, stir and heat up to 50°C, keep stirring for 15 minutes to obtain a mixed solution M; Add 8.0kg of formic acid dropwise, and drop it for about 30 minutes. After 2 hours of heat preservation, the mixed solution N is obtained; the solution N is sampled and tested, and when the test result shows that there is no 2-(3-nitrophenyl)imidazoline residue in the solution N , then the solution N is cooled to below 40 DEG C and filtered, and the catalyst palladium charcoal is rinsed with an appropriate amount of water, and the filtrate is put into a still kettle and added an appropriate amount of water to carry out distillation to evaporate the organic solvent methanol ...

Embodiment approach 3

[0043] 1. Preparation of 2-(3-nitrophenyl)imidazoline: the preparation method is the same as in Embodiment 1.

[0044] Two, prepare 2-(3-aminophenyl) imidazoline hydrochloride:

[0045] Put 6kg of 2-(3-nitrophenyl) imidazoline, 0.6kg of palladium carbon and 60L of methanol aqueous solution into a 100L enamel reaction kettle, stir and heat up to 65°C, keep stirring for 15 minutes to obtain a mixed solution M; Add 10.0kg of formic acid dropwise, drop it for about 30 minutes, and get a mixed solution N after keeping it warm for 2 hours; take a sample of the solution N, and when the test result shows that there is no 2-(3-nitrophenyl)imidazoline residue in the solution N , then the solution N is cooled to below 40 DEG C and filtered, and the catalyst palladium charcoal is rinsed with an appropriate amount of water, and the filtrate is put into a still kettle and added an appropriate amount of water to carry out distillation to evaporate the organic solvent methanol in the filtrate...

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PUM

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Abstract

The invention relates to the field of chemical engineering and discloses a preparation method of 2-(3-amino phenyl) imidazoline hydrochloride and imidocarb. The preparation method comprises the following steps of: inputting 2-(3-nitryl phenyl) imidazoline, a catalyst and an alcohol-water mixed solution into a reaction kettle, stirring the mixture and raising the temperature to 50-65 DEG C, keeping the temperature and stirring the mixture for 10-20 min to obtain a mixed solution M; dropwise adding formic acid into the solution M, and keeping the temperature to react for 1.5-2.5h to obtain a mixed solution N; cooling the solution N to 40 DEG C below and filtering the solution, and evaporating alcohol to obtain a 2-(3-amino phenyl) imidazoline aqueous solution; dropwise adding hydrochloric acid into the 2-(3-amino phenyl) imidazoline aqueous solution to be neutral; and performing crystallization, suction filtration, pressure reduction and drying to obtain a target product 2-(3-amino phenyl) imidazoline hydrochloride. Compared with catalytic hydrogenation in the prior art, by taking formic acid as a hydrogen donor for transfer hydrogenation, the product purity and yield are of no obvious differences but no safety risks are available, and the preparation method is free of special demand, easy to operate and convenient for production and application.

Description

technical field [0001] The invention relates to the field of chemical industry, in particular to a preparation method of 2-(3-aminophenyl) imidazoline hydrochloride and imidazolium. Background technique [0002] Imidazole is a chemical used in veterinary medicine. It is an anti-piriform drug diphenylurea diamidine derivative. It is an important compound with biological activity. Generally, imidazole dihydrochloride and imidazole dipropane Salts are the most common. They have the advantages of broad spectrum, low toxicity, wide application range, long action time, and small dosage. Also has a good preventive effect. [0003] The imidazolium synthesis process is mainly to prepare 2-(3-nitrophenyl)imidazoline, 2-(3-nitrophenyl)imidazoline through the reflux reaction of m-nitrobenzonitrile and ethylenediamine under catalytic conditions. After reduction, 2-(3-aminophenyl) imidazoline is obtained, and 2-(3-aminophenyl) imidazoline reacts with diphosgene to obtain imidazolium. ...

Claims

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Application Information

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IPC IPC(8): C07D233/24
CPCC07D233/24
Inventor 张守平
Owner GUANNAN YISITE CHEM
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