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Preparation method of imidocarb

A technology of imidazobenzene urea and imidazoline, which is applied in the field of pharmaceutical chemical preparation, can solve the problems of long production cycle, difficult separation of material and liquid, slow speed, etc., and achieves the advantages of simple and convenient post-processing operation, overcoming complicated operation and easy reaction process. Effect

Active Publication Date: 2013-02-13
QILU ANIMAL HEALTH PROD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The disadvantage of the above method is that the preparation process of imidazuron 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 is low; the production cycle is long, energy consumption is large, and the cost High, limiting the scale of industrial production

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0043] A preparation method of imidazolium, the steps are as follows:

[0044] (1) Add 121.0 kg of m-nitrobenzoic acid and 344.9 kg of thionyl chloride into the reaction kettle, mix and stir and heat up to 80°C, reflux for 4 hours, concentrate under reduced pressure at 75°C under temperature control to remove thionyl chloride, and prepare at room temperature Obtain m-nitrobenzoyl chloride 134.1kg, this m-nitrobenzoyl chloride yellow solid, molar yield 99.8%;

[0045] (2) Add 133.3kg of m-nitrobenzoyl chloride prepared in step (1) into 600L of acetonitrile, then add 8.0kg of molybdophosphovanadate heteropolyacid, stir and add 47.3kg of ethylenediamine, stir and heat up to 80°C, reflux React for 2 hours, filter, take the filtrate, and concentrate under reduced pressure at 75°C to obtain 126.5kg of yellow-green 2-(3-nitrophenyl)imidazoline solid with a molar yield of 91.6%.

[0046] (3) Add 124.4kg of 2-(3-nitrophenyl)imidazoline prepared in step (2) into 600L of water, and then...

Embodiment 2

[0050] Preparation method as described in Example 1, the difference is that,

[0051](4) Add 122.4kg of the prepared 2-(3-aminophenyl)imidazoline hydrochloride into 700LN,N-methylformamide, stir and add 33kg of urea, stir and heat up to 155°C, react for 4.5h, and cool down to 0°C, stand for crystallization for 1 hour, filter and wash, and vacuum-dry at 60°C to obtain 91.5 kg of imidazolium as a white solid.

[0052] After testing, the prepared imidazuron mp (melting point) is 350-352°C, the content is 98.9%, and the molar yield is 83.8%.

Embodiment 3

[0054] Preparation method as described in Example 1, the difference is that,

[0055] (4) Add 120.5kg of the prepared 2-(3-aminophenyl)imidazoline hydrochloride into 700LN,N-dimethylformamide, stir and add 33kg of urea, stir and heat up to 160°C, react for 5h, and cool down to 3°C, stand for crystallization for 1 hour, filter and wash, and vacuum-dry at 60°C to obtain 89.7 kg of imidazolium as a white solid.

[0056] After testing, the prepared imidazuron mp (melting point) is 350-352°C, the content is 99.1%, and the molar yield is 83.7%.

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Abstract

The invention relates to a preparation method of imidocarb. The preparation method of the imidocarb comprises the following steps: (1) mixing nitrobenzoic acid with thionyl chloride and obtaining nitrobenzoyl chloride by carrying out a reflux reaction of the nitrobenzoic acid and the thionyl chloride, (2) adding the nitrobenzoyl chloride into acetonitrile and then adding P-Mo-V heteropolyacid and ethylenediamine, obtaining 2-(3-nitrophenyl) imidazoline by carrying out the reflux reaction of the nitrobenzoyl chloride, acetonitrile, the P-Mo-V heteropolyacid and the ethylenediamine (3) adding the 2-(3-nitrophenyl) imidazoline into a solvent, adding palladium carbon, and obtaining 2-(3-nitrophenyl) imidazoline hydrochloride by carrying out a reduction hydrogenation reaction of the 2-(3-nitrophenyl) imidazoline, the solvent and the palladium carbon, (4) adding the 2-(3-nitrophenyl) imidazoline hydrochloride into N-dimethylformamide, stirring and adding urea, and obtaining the imidocarb by carrying out a reaction of the 2-(3-nitrophenyl) imidazoline hydrochloride, N-dimethylformamide and urea for 4.5-5.5 hours. According to the method, purity of imidocarb liquid is more than 99%, and molar yield is stabilized at more than 71% and higher than the existing highest yield of 65%.

Description

technical field [0001] The invention relates to a method for preparing imidazuron, which belongs to the technical field of preparation of medicinal chemicals. Background technique [0002] 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 No. 3,338,917 describes the method for preparing imidazolium hydrochloride from 2-(3-aminophenyl) imidazoline dihydrochloride, that is, in 2-(3-aminophenyl) imidazoline dihydrochloride aqueous solution, pass into phosgene reaction , to obtain imidazolium hydrochloride through separation and preparation. [0004] Chinese patent CN1850805A (application numb...

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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