Chemical synthesis method for 2-imidazole alkyl ketone

A technology of imidazolidinone and chemical synthesis, applied in the direction of organic chemistry, can solve the problems of deep side reactions, difficult refining, high production cost, etc., and achieve the effect of mild reaction conditions, advanced process route and low production cost

Active Publication Date: 2008-09-24
浙江遂昌利民科技有限公司
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  • Abstract
  • Description
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Problems solved by technology

[0004] Among the above methods, although the phosgene method has the advantages of mild reaction conditions, fast reaction speed, convenient refining, and high yield, due to the use of highly toxic raw material phosgene, on the one hand, there is a big safety hazard, and the by-product hydrogen chloride containing phosgene is recycled. Difficult. On the other hand, phosgene is highly active and prone to deep side reactions, which brings certain difficulties to product post-processing, high production costs, and a large amount of three wastes
The urea method must adopt temperature programming in the reaction process, the production process is difficult to control, and the product quality is poor due to polymer impurities, and the refining is very difficult

Method used

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  • Chemical synthesis method for 2-imidazole alkyl ketone
  • Chemical synthesis method for 2-imidazole alkyl ketone

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Feed ratio ethylenediamine: bis (trichloromethyl) carbonate is 3: 1 (molar ratio), and toluene is used as solvent, and its consumption is 12mL / g in terms of ethylenediamine quality; Tetrabutylammonium bromide is phase transfer Catalyst, the dosage is 0.05 times of the mass of ethylenediamine.

[0025] In a four-neck flask equipped with mechanical stirring, reflux condenser, thermometer and constant pressure titration funnel, add ethylenediamine (9 g, 150 mmol), 10% aqueous sodium hydroxide solution (120 mL), toluene (48 mL) and tetrabutyl ammonium bromide (1.35 g, 4.2 mmol), and mechanical stirring was started. 1 Slowly add a solution of bis(trichloromethyl)carbonate (14.7 g, 49 mmol) dissolved in toluene (60 mL) dropwise at around 5°C for 6 hours. After the dropwise addition was completed, the reaction was carried out at room temperature for 3h. After the reaction, the reaction solution was allowed to stand still and separated into layers, and the water layer was sep...

Embodiment 2

[0028] Feed ratio ethylenediamine: bis(trichloromethyl)carbonate is 3: 1 (molar ratio), toluene is used as solvent, and its consumption is 12mL / g in terms of ethylenediamine mass, tetrabutylammonium chloride is phase transfer Catalyst, the dosage is 0.05 times of the mass of ethylenediamine. The feeding amount of ethylenediamine is 150mmol, the feeding amount of bis(trichloromethyl)carbonate is 49mmol, and the adding time of bis(trichloromethyl)carbonate is 1h.

[0029] The recrystallization solvent was changed to methanol, and other operations were the same as in Example 1. The product yield was 73.1%, melting point: 130.6° C., and purity 98.0%.

Embodiment 3

[0031] Feed ratio ethylenediamine: bis(trichloromethyl) carbonate is 3: 1 (molar ratio), toluene is used as solvent, and its consumption is 12mL / g based on ethylenediamine mass, and tetrabutylammonium bromide is phase The transfer catalyst is used in an amount of 0.05 times the mass of ethylenediamine. The feeding amount of ethylenediamine is 150mmol, the feeding amount of bis(trichloromethyl)carbonate is 49mmol, the time for adding bis(trichloromethyl)carbonate is 1h, the concentration of aqueous sodium hydroxide solution is 5%, and the consumption is 240mL .

[0032] Other operations are the same as in Example 1, the product yield is 75.4%, the melting point is 129.6° C., and the purity is 98.3%.

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Abstract

The present invention discloses a chemical synthetic method of 2-imidazole flavanone. The synthetic method comprises the following steps: ethylenediamine and 2 to 20 percent of sodium hydroxide solution are added in a reactor; at the temperature from minus 10 DEG C to 50 DEG C, bi(trichloromethyl) carbonate is slowly dropped into the reactor for 1 to 15 hours; then the mixture reacts for 1 to 20 hours at the temperature from 0 DEG C to 80 DEG C; after the reaction, the reaction solution can be treated to prepare the 2-imidazole flavanone. The chemical synthetic method has high yield (generally above 80 percent) and high purity (generally above 98.0 percent). Thus the chemical synthetic method is an effective synthetic method with reasonable process, low production cost, high yield and less three-waste.

Description

(1) Technical field [0001] The invention relates to a chemical synthesis method of 2-imidazolidinone. (2) Background technology [0002] In the pharmaceutical industry, 2-imidazolidinone is the key intermediate of many new antibiotics, such as mezlocillin and azlocillin, and can be used as the basic raw material of the third generation penicillin, and can also be used as the intermediate of anti-schistosomiasis drugs . In addition, this product has a unique effect on removing formaldehyde. It can also effectively remove formaldehyde remaining in fabrics after finishing with 2D-resin, KB resin, urea-formaldehyde resin, melamine-formaldehyde resin, etc., so it can also be used to synthesize high-performance formaldehyde scavenger , home air formaldehyde powerful enzymes, etc.; in the biological field, it can produce plant growth regulators, fungicides, inhibitors, herbicides, etc. [0003] Before the present invention was made, the chemical synthesis methods of 2-imidazolidi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/70
Inventor 苏为科李振华梁现蕊李峰濮发祥
Owner 浙江遂昌利民科技有限公司
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