Preparation method of 4-phenylimidazole

A technology of phenylimidazole and temperature control, which is applied in the direction of organic chemistry, can solve the problem of no cost advantage, and achieve the effect of convenient product purification, less reaction steps and simple process

Inactive Publication Date: 2015-07-15
ZHANGJIAGANG XINYI CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Ten Have, Ronald et al. synthesized 4-phenylimidazole (Tetrahedron, Vol.53, P11355) by reacting p-toluenesulfonylmethyl isonitrile and p-toluenesulfonyl benzimide, and the yield was 75%, but the literature Raw materials are unconventional raw materials and have no advantage in cost

Method used

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  • Preparation method of 4-phenylimidazole

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Embodiment 1

[0026] 1) Substitution: Add 200ml of ethylene glycol to a four-neck flask, raise the temperature to 50°C, slowly add 50g of α-bromoacetophenone (0.25mol) while stirring, and control the temperature at 50±2°C during the addition process. After 30 minutes of heat preservation, slowly add 55g of formamidine acetate (0.53mol) at 50±2°C for 45 minutes, and continue to react at 50±2°C for 2 hours after the addition.

[0027] 2) Cycling: Cool down to 30°C, slowly add 130g (0.94mol) of potassium carbonate, and finish adding in 1 hour, continue to keep warm at 32±2°C for 6 hours, then rapidly raise the temperature to 82±2°C, and keep warm for 5 hours. The reaction is over.

[0028] 3) Post-processing: slowly turn on the vacuum pump, and distill ethylene glycol under reduced pressure. Control the low vacuum at the beginning, increase the vacuum after the discharge is slow, maintain the vacuum degree of 15mmHg, and finally distill the ethylene glycol at 145 degrees Celsius. Steam out. ...

Embodiment 2

[0030] 1) Substitution: Add 220ml of ethylene glycol to a four-neck flask, raise the temperature to 50°C, slowly add 50g of α-bromoacetophenone (0.25mol) while stirring, and control the temperature at 55±2°C during the addition process. After 30 minutes of heat preservation, slowly add 54g of formamidine acetate (0.52mol) at 55±2°C for 60 minutes, and continue to react at 55±2°C for 2 hours after the addition.

[0031] 2) Cycling: Cool down to 30°C, slowly add 130g (0.94mol) of potassium carbonate, and finish adding in 1 hour, continue to keep warm at 32±2°C for 5 hours, then quickly raise the temperature to 86±2°C, and keep warm for 6 hours. The reaction is over.

[0032] 3) Post-processing: slowly turn on the vacuum pump, and distill ethylene glycol under reduced pressure. Control the low vacuum at the beginning, increase the vacuum after the discharge is slow, maintain the vacuum degree of 15mmHg, and finally distill the ethylene glycol at 148 degrees Celsius. Steam out. ...

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Abstract

The invention discloses a preparation method of 4-phenylimidazole. The method comprises the following steps: 1) substitution, namely, dissolving alpha-bromoacetophenone into formamidine acetate, and reacting in ethylene glycol, so as to obtain a nucleophilic replace intermediate; 2) cyclizing, namely, adding potassium carbonate as an acid-binding agent, and controlling the temperature to carry out a cyclization reaction; and 3) post-treatment, namely obtaining the 4-phenylimidazole by post-treatment after the reaction is ended. According to the technical scheme disclosed by the invention, the 4-phenylimidazole is synthetized from conventional chemical raw materials; the preparation method is simple in process, less in reaction steps, and convenient to purify; an industrial operation is facilitated; the target product is white in color and luster; the content of the final product can be up to over 99%; the yield is greater than 45%.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and relates to a method for preparing 4-phenylimidazole by a one-pot synthesis method. Background technique [0002] As the basic raw material of drugs for central nervous system and metabolic disorders (WO2011 / 150156, WO2013 / 50527, WO2004 / 74283, etc.), 4-phenylimidazole is widely used in the pharmaceutical industry, but the synthesis and application of this product started relatively late in China. There are few reports on the synthesis and research of this product at present. Bredereck.H. published an article in 1953 (Chem.Ber.Vol.86, P88) using α-bromoacetophenone and formamide as raw materials to synthesize 4-phenylimidazole, and the literature shows that the yield is as high as 90%. But Dr. Benjes, P.A. can only obtain the product of 25% yield by the same method (Benjes, P.A., Ph.D.Thesis, University of Otago, New Zealand, 1994). [0003] Chem.Ber., 86, P96 reacts with formamide w...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/58
Inventor 楼新灿王强
Owner ZHANGJIAGANG XINYI CHEM
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