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Preparation method of imidocarb

A technology of imidazolium and imidazoline, which is applied in the field of preparation of pharmaceutical chemicals, can solve the problems of long production cycle, difficult material-liquid separation, slow rate, etc., and achieve the advantages of simple post-treatment operation, overcoming cumbersome operation, and easy reaction process Effect

Active Publication Date: 2014-12-31
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 imidazolide, the steps are as follows:

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

[0045] (2) Add 133.3kg of m-nitrobenzoyl chloride prepared in step (1) to 600L acetonitrile, then add 8.0kg of phosphomolybdovanadium heteropoly acid, stir and add 47.3kg of ethylenediamine, stir and heat to 80°C, reflux The reaction was carried out for 2 hours, filtered, and the filtrate was taken and concentrated under reduced pressure at 75°C to obtain 126.5 kg of yellow-green 2-(3-nitrophenyl) imidazoline solid with a molar yield of 91.6%.

[0046] (3) Add 124.4 kg of 2-(3-nitrophenyl) imidazoline prepared in s...

Embodiment 2

[0050] The preparation method as described in Example 1, except that:

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

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

Embodiment 3

[0054] The preparation method as described in Example 1, except that:

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

[0056] After testing, the prepared imidazocarb 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 preparation method of imidazole carbamide and belongs to the technical field of preparation of medicinal chemicals. Background technique [0002] Imidazole carbamide is a derivative of s-diphenylurea and is a new type of antiprotozoal chemical medicine for animals. In clinical practice, its dipropionate or dihydrochloride is generally used as a preparation, which can be injected into the muscle or subcutaneously to treat and prevent various Babesiosis, Pyriformis, Trypanosomiasis, and eperythrocytes Disease, borderworm disease and Taylor's disease. [0003] US Patent No. 3,338,917 describes a method for preparing imidazolide hydrochloride from 2-(3-aminophenyl)imidazoline dihydrochloride, that is, in the aqueous solution of 2-(3-aminophenyl)imidazoline dihydrochloride, phosgene is reacted. , After separation and preparation to obtain imidazolide hydrochloride. [0004] Chinese patent CN1850805A (application number: 200610083133.5) ...

Claims

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Application Information

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Patent Type & Authority Patents(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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