Preparation method of imidocarb dipropionate and intermediate thereof

A technology of imidazolium dipropionate and intermediates, which is applied in the field of preparation of imidazolium dipropionate, can solve the problems of not conforming to the concept of green synthesis, not suitable for industrial production, and high toxicity of diphosgene, and achieve the reduction of solid Effects of waste generation, ease of operation, and shortened reaction time

Inactive Publication Date: 2020-08-25
SHANDONG ACADEMY OF PHARMACEUTICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When this route uses sulfur as a catalyst, sublimed sulfur will condense in the condenser pipe when it is refluxed, thereby blocking the condenser pipe, reducing iron powder to produce a large amount of iron sludge, which pollutes the environment, and diphosgene is highly toxic, which does not conform to the concept of green synthesis and is not suitable for industrial production.

Method used

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  • Preparation method of imidocarb dipropionate and intermediate thereof
  • Preparation method of imidocarb dipropionate and intermediate thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Synthesis of compound 3

[0025] Add 1L of methanol into a 2L three-necked reaction flask, add m-nitrobenzonitrile (100g, 0.67mol) under stirring, Na 2 S (26.35g, 0.335mol) and ethylenediamine (48.65g, 0.81mol) were heated and stirred to reflux. Reflux for 8 hours, heat filter, cool the filtrate to -5°C ~ 0°C, stir and crystallize for 2 hours, filter, wash the filter cake with a small amount of cold methanol, and dry the product in vacuum to obtain light yellow solid 2-(3-nitrophenyl) Imidazoline (123 g, 95.3%).

Embodiment 2

[0027] Synthesis of compound 3

[0028] Add 1L of methanol into a 2L three-necked reaction flask, add m-nitrobenzonitrile (100g, 0.67mol) under stirring, Na 2 S (52.7g, 0.67mol) and ethylenediamine (48.65g, 0.81mol) were heated and stirred to reflux. Reflux for 8 hours, heat filter, cool the filtrate to -5°C ~ 0°C, stir and crystallize for 2 hours, filter, wash the filter cake with a small amount of cold methanol, and dry the product in vacuum to obtain light yellow solid 2-(3-nitrophenyl) Imidazoline (120 g, 93.2%).

Embodiment 3

[0030] Synthesis of Compound 4

[0031] Add 1L of water, 2-(3-nitrophenyl)imidazoline (120g, 0.63mol) into a 3L reaction flask, carefully add 3.6g of 10% wet palladium carbon, slowly raise the temperature and stir to reflux, slowly add formic acid dropwise A solution of ammonium (119.7g, 1.89mol) in water (240mL) was added for about 0.5h, kept warm for 2h, filtered to obtain a light yellow clear liquid, and the filtrate was directly injected into the next step.

[0032] Synthesis of compound 5

[0033] Add the reaction solution from the previous step, hydrochloric acid (134mL, 1.6mol), and urea (19.2g, 0.32mol) into a 2L three-necked reaction flask in turn, heat and stir until reflux under nitrogen protection, keep the reaction for 8h, and cool the reaction solution to room temperature. / L of sodium hydroxide aqueous solution to adjust the pH to 9-10, a large amount of white solids precipitated, stirred at room temperature for 0.5h, filtered, washed the filter cake with a sma...

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Abstract

The invention discloses a preparation method of imidocarb dipropionate and an intermediate thereof and belongs to the technical field of chemical pharmacy. According to the method, m-nitrobenzonitrilereacts with ethylenediamine with sodium sulfide taken as a catalyst; palladium on carbon-ammonium formate reduction is performed; a product and urea are subjected to condensation reaction, so that imidazole phenylurea dihydrochloride can be obtained; dissociated imidazole phenylurea reacts with propionic acid, so that the imidazole phenylurea dipropionate can be obtained. The method has the advantages o reduced wastes, cheap and easily available raw materials, simple operation, high product yield, simple process operation and high safety, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of chemical pharmacy, and in particular relates to a preparation method of imidazolium dipropionate. Background technique [0002] Piroplasmosis is a general term for a class of blood protozoa diseases transmitted by hard ticks and caused by Piroplasma Babesco or Thaleridae. It usually spreads among domestic animals and wild mammals. It is very common in many countries in the world, including China. The epidemic has caused great losses to the world animal husbandry and the world economy. [0003] The diphenylurea bismidazolium compound imidazolium (chemical name N,N'-bis[3-(4,5-dihydro-1H-imidazol-2-yl)phenyl]urea with all hydrogen substituents ), is the best anti-piriform drug of a new generation, and its structural formula is as follows: [0004] [0005] Developed by the Swiss company Monbijoustrasse, its dihydrochloride was first launched in Switzerland in 1969 and has important biological activity....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/64C07C51/41C07C53/122B01J27/04
CPCC07D233/64C07C51/412B01J27/04
Inventor 孔祥雨杨利崔新强樊志萍张彬李新志刘文涛段崇刚崔燕任业明
Owner SHANDONG ACADEMY OF PHARMACEUTICAL SCIENCES
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