Preparation method of 2-(3-aminophenyl) imidazoline hydrochloride

A technology of imidazoline hydrochloride and aminophenyl, which is applied in the field of preparation of 2-imidazoline hydrochloride, can solve the problems of limited industrial production scale, difficult separation of material and liquid, complicated preparation process and the like, and achieves good industrialization prospects , Overcome the cumbersome operation and the effect of environmental friendliness

Active Publication Date: 2013-01-30
QILU ANIMAL HEALTH PROD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The defect of said method is that the preparation process of 2-(3-aminophenyl) imidazoline hydrochloride is cumbersome to operate, and wastes such as iron sludge are produced, and the separation of material and liquid is difficult; the reaction process is difficult to control, and the rate is slow, and the yield Low; long production cycle, high energy consumption, high cost, limiting the scale of industrial production

Method used

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  • Preparation method of 2-(3-aminophenyl) imidazoline hydrochloride

Examples

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Embodiment 1

[0031] A kind of preparation method of 2-(3-aminophenyl) imidazoline hydrochloride, the steps are as follows:

[0032] Dissolve 124.4 kg of 2-(3-nitrophenyl) imidazoline in 600 L of water and add it to the hydrogenation kettle, then add 10.0 kg of palladium-carbon catalyst containing 5 wt% palladium, seal the hydrogenation kettle, and pass nitrogen gas 3 times to drain Air and check air tightness, replace nitrogen with hydrogen for 3 times, keep the pressure constant to 0.3MPa, control the reaction temperature at 50°C to 55°C, carry out reduction hydrogenation reaction for 3 hours, replace hydrogen with nitrogen for 3 times, filter the reaction solution, and recover palladium Carbon, take the light yellow filtrate, adjust the pH to 2.0 with 6mol / L hydrochloric acid, cool down to 0°C, let stand for crystallization for 1h, filter to obtain a white solid, and vacuum-dry at 60°C for 8 hours to obtain 122.1kg of an off-white solid.

[0033] After testing, the mp (melting point) is ...

Embodiment 2

[0035] A kind of preparation method of 2-(3-aminophenyl) imidazoline hydrochloride, the steps are as follows:

[0036] 126.5 kg of 2-(3-nitrophenyl) imidazoline was dissolved in 600L ethanol and added to the hydrogenation kettle, and then 10.0 kg of palladium-carbon catalyst containing 5 wt % of palladium was added, and the palladium-carbon catalyst containing 5 wt % of palladium was In order to adopt the method of Example 1 to recycle the catalyst after 5 times, seal the hydrogenation tank, pass nitrogen 3 times to discharge the air and check the air tightness, replace the nitrogen with hydrogen 3 times, keep the constant pressure to 0.01MPa, and control the reaction The temperature is 30°C to 35°C, carry out the reduction hydrogenation reaction for 6 hours, replace the hydrogen with nitrogen for 3 times, filter the reaction solution, recover palladium carbon, take the light yellow filtrate, adjust the pH to 2.0 with 6mol / L hydrochloric acid, and cool down to -2°C , standing ...

Embodiment 3

[0039] A kind of preparation method of 2-(3-aminophenyl) imidazoline hydrochloride, the steps are as follows:

[0040] 2-(3-nitrophenyl) imidazoline 125.0kg is dissolved in 600L water and adds in the hydrogenation kettle, then adds palladium carbon catalyst 10.0kg containing palladium amount 5wt%, the palladium carbon catalyst containing palladium amount 5wt% is Adopt the method of Example 1 to recycle the catalyst after 7 times, seal the hydrogenation tank, pass nitrogen 3 times to discharge the air and check the air tightness, replace the nitrogen with hydrogen 3 times, keep the constant pressure to 0.1MPa, and control the reaction temperature at 40°C to 45°C, carry out reductive hydrogenation reaction for 4.5 hours, replace hydrogen with nitrogen for 3 times, filter the reaction solution, recover palladium carbon, take light yellow filtrate, adjust pH=2.0 with 6mol / L hydrochloric acid, cool to 3°C, and statically Set aside for crystallization for 1 h, filter to obtain a whi...

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Abstract

The invention relates to a preparation method of 2-(3-aminophenyl) imidazoline hydrochloride. the method comprises the steps of: adding 2-(3-aminophenyl) imidazoline to a solvent according to a mass-volume ratio of 1:(2-1); then adding palladium carbon with the palladium content of 0.5-10wt% in the proportion of 1-10% of the weight of the 2-(3-aminophenyl) imidazoline; carrying out reducing hydrogenation reaction for 2.5-6 hours under the conditions that the temperature is 10-100 DEG C, the atmosphere is hydrogen and the pressure of 0.01-0.95MPa; filtering, adjusting the pH of a filtrate to be at 1.0-3.0, reducing the temperature to -2-3 DEG C, standing for crystallization for 0.5-2h, filtering to obtain a precipitate, and drying the precipitate to prepare the 2-(3-aminophenyl) imidazoline hydrochloride. The preparation method is easy to control, small in energy consumption, low in cost, environment-friendly, and good in industrialization prospect.

Description

technical field [0001] The invention relates to a preparation method of 2-(3-aminophenyl)imidazoline hydrochloride, belonging to the technical field of veterinary drug preparation. Background technique [0002] 2-(3-Aminophenyl)imidazoline hydrochloride is a necessary intermediate for the preparation of imidazolium. Imidazuron belongs to the derivative of diphenyl urea, which is a new type of anti-protozoal chemical drug specially used for animals. Clinically, its dipropionate or bishydrochloride is commonly used to make preparations, which are injected intramuscularly or subcutaneously to treat and prevent various babesiosis, piriplasmosis, trypanosomiasis, and eperythrocytic disease, borderworm disease and theileriasis, etc. [0003] U.S. patent document US3338917 discloses the method that 2-(3-aminophenyl) imidazoline dihydrochloride prepares imidazolium hydrochloride, that is, in 2-(3-aminophenyl) imidazoline dihydrochloride aqueous solution, pass into phosgene Conden...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/24
Inventor 苏玉辉方明锋刘全才孔梅吴连勇
Owner QILU ANIMAL HEALTH PROD
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