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Preparation method of imidocarb

A technology of imidazobenzeneurea and nitroimidazoline, which is applied in the field of compound synthesis, can solve the problems of high energy consumption, long production cycle, and many wastes, and achieves the effects of mild reaction conditions, convenient operation and pollution avoidance.

Active Publication Date: 2014-07-02
山东久隆精细化工有限公司 +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The defect of the above method is that the preparation process of imidazuron is cumbersome, and there are many wastes and heavy pollution.
The production cycle is long, the reaction yield is low, the energy consumption is high, and industrial production is difficult

Method used

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  • Preparation method of imidocarb
  • Preparation method of imidocarb
  • Preparation method of imidocarb

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Dissolve 18.1 g of methyl m-nitrobenzoate, 6.0 g of ethylenediamine, and 0.16 g of sulfur in 110 ml of methanol, reflux at 65°C for 4 hours, evaporate most of the solvent under reduced pressure, and filter to obtain m-nitroimidazoline , and the molar yield was 95.0%.

[0024] Take 17.2g of the intermediate product m-nitroimidazoline, dissolve it in 90ml of 50% methanol, adjust the pH value to 4.0 with 5mol / L hydrochloric acid, and add 7.0g of zinc powder while stirring in four times at normal temperature within 2 hours, and the addition is completed. The stirring reaction was continued for 1 hour. After the reaction was finished, the zinc chloride was removed by filtration, most of the solvent was evaporated under reduced pressure, and the crystallized m-aminoimidazoline had a molar yield of 91.3%.

[0025] Then take 13.0g of m-aminoimidazoline and dissolve it in 65ml of tetrahydrofuran-water (1:5) solution, adjust the pH value to 8 with 0.1mol / L sodium hydroxide solut...

Embodiment 2

[0027] Dissolve 18.1 g of methyl m-nitrobenzoate, 9.0 g of ethylenediamine, and 0.16 g of sulfur in 110 ml of methanol, reflux at 65°C for 5 hours, evaporate most of the solvent under reduced pressure, and filter to obtain m-nitroimidazoline , and the molar yield was 95.1%.

[0028] Then take 17.2g of the intermediate product m-nitroimidazoline, dissolve it in 90ml of 50% methanol, adjust the pH value to 3.5 with 5mol / L hydrochloric acid, add 8.0g of zinc powder while stirring in four times at normal temperature within 2 hours, and complete the addition. The stirring reaction was continued for 2 hours. After the reaction was finished, zinc chloride was removed by filtration, most of the solvent was evaporated under reduced pressure, and the crystallized m-aminoimidazoline had a molar yield of 91.7%.

[0029] Dissolve 13.0 g of m-aminoimidazoline in 65 ml of tetrahydrofuran-water (1:5, V:V) solution, adjust the pH value to 10 with 0.1 mol / l sodium hydroxide solution, add 0.08 ...

Embodiment 3

[0031] Take 18.1g of methyl m-nitrobenzoate, 4.0g of ethylenediamine, and dissolve 0.32g of sulfur in 181ml of methanol. After reflux at 65°C for 3 hours, add 2.0g of ethylenediamine and reflux for 2 hours, and distill out under reduced pressure. After removing most of the solvent, m-nitroimidazoline was obtained by filtration with a molar yield of 96.4%.

[0032] Then take 17.2g of the intermediate product m-nitroimidazoline, dissolve it in 90ml of 50% methanol, add 5mol / L hydrochloric acid to adjust the pH value to 3.5, add 8.8g of zinc powder while stirring in four times at normal temperature within 2 hours, and complete the addition The stirring reaction was continued for 2 hours. After the reaction was finished, the zinc chloride was removed by filtration, most of the solvent was evaporated under reduced pressure, and the crystallized m-aminoimidazoline had a molar yield of 92.0%.

[0033] Dissolve 13.0 g of m-aminoimidazoline in 65 ml of tetrahydrofuran-water (1:6, V:V)...

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Abstract

The invention relates to a preparation method of imidocarb. The preparation method comprises the steps of dissolving methyl-m-nitrobenzoate into a solvent, enabling methyl-m-nitrobenzoate and ethylenediamine to be subjected to cyclization reaction at the temperature of 55-65 DEG C for 3-6h under the action of a catalyst, and separating to prepare m-nitroimidazoline; dissolving m-nitroimidazoline into a water solution of methanol, adding zinc powder under an acidic condition, after the addition is ended, carrying out reduction reaction for 1-2h while stirring at normal temperature, and separating and purifying to prepare m-aminoimidazoline; dissolving m-aminoimidazoline into a water solution of tetrahydrofuran, regulating the pH value to 7-10, adding triphosgene, reacting at the temperature of 10-40 DEG C for 2-6h, filtering and drying to obtain imidocarb. Methyl-m-nitrobenzoate is used as a starting raw material, and zinc powder is used as a reducing agent, so that the preparation method is mild in reaction condition, convenient in operation and relatively low in cost.

Description

technical field [0001] The invention relates to a method for preparing imidazuron, which belongs to the technical field of compound synthesis. Background technique [0002] Imidazuron 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, dihydrochloride and dipropionate 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] U.S. Patent US3338917 introduces a synthetic method of preparing imidazolium by reacting 2-(3-aminophenyl) imidazoline with phosgene; gas to form a diphenylurea structure, and then react with ethylenediamine to prepare imidazole urea; Chinese patent CN101348465A introduces a method that uses m-nitrobenzonitrile as a raw material, and first reacts with ethylenediamine to prepare m-nitroimidazoline. Then it is red...

Claims

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Application Information

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IPC IPC(8): C07D233/24
CPCC07D233/24
Inventor 周金华李志远樊亚丽
Owner 山东久隆精细化工有限公司
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