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Synthesis method of iminostilbene

An iminostilbene and synthesis method technology, applied in the direction of organic chemistry and the like, can solve the problems of heavy pollution, long steps, low yield and the like, and achieve the effects of optimizing reaction conditions and shortening reaction steps.

Inactive Publication Date: 2013-09-11
CHANGZHOU UNIV
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  • Abstract
  • Description
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AI Technical Summary

Problems solved by technology

[0005] In order to solve the above problems, i.e. long steps, heavy pollution, low yield, etc., the present invention provides a simple method for synthesizing the compound iminostilbene with high yield and low cost

Method used

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  • Synthesis method of iminostilbene
  • Synthesis method of iminostilbene

Examples

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Effect test

example 1

[0021] Add 6.65 g (0.025 mol) of 2-(dichlorotoluene) diphenylamine, 0.14 g (0.0012 mol) of L-proline and 10 mL of absolute ethanol to a 100 mL four-necked flask in sequence. Stir and keep the temperature at 20-40°C, add potassium hydroxide absolute ethanol solution (containing 2.80g, 0.05molKOH, 27.50mL CH 3 CH 2 OH). The reaction time is 5-12 hours. Filter, wash the brown solid with absolute ethanol three times, extract with hot ethyl acetate, cool, the solid precipitates, and recrystallize with toluene to obtain 2.19 g of a golden yellow solid with a yield of 45.38%.

example 2

[0023] Add 8.87 g (0.025 mol) of 2-(dibromotoluene) diphenylamine, 0.58 g (0.0050 mol) of L-proline and 20 mL of absolute ethanol to a 100 mL four-neck flask in sequence. Stir and keep the temperature at 20-40°C, add potassium hydroxide absolute ethanol solution (containing 7.01g, 0.12molKOH, 42.50mL CH 3 CH 2 OH). The reaction time is 5-12 hours. Filter, wash the brown solid with absolute ethanol three times, extract with hot ethyl acetate, cool, the solid precipitates, and recrystallize with toluene to obtain 2.92 g of a golden yellow solid with a yield of 60.51%.

example 3

[0025] 11.22 g (0.025 mol) of 2-(diiodotoluene) diphenylamine, 0.44 g (0.0038 mol) of L-proline and 20 mL of absolute ethanol were sequentially added into a 100 mL four-necked flask. Stir and keep the temperature at 20-40°C, add potassium hydroxide absolute ethanol solution (containing 4.90g, 0.087molKOH, 30mL CH 3 CH 2 OH). The reaction time is 5-12 hours. Filter, wash the brown solid with absolute ethanol three times, extract with hot ethyl acetate, cool, the solid precipitates, and recrystallize with toluene to obtain 3.90 g of a golden yellow solid with a yield of 80.82%.

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Abstract

The invention discloses a synthesis method of iminostilbene, belonging to the field of drug synthesis. The method comprises the following steps of: in the presence of a phase transfer catalyst and alkali, heating a compound for coupling in an organic solvent to obtain iminostilbene. The invention provides a novel method for synthesizing iminostilbene, and the reaction conditions are optimized so that the reaction can be performed at a low temperature; and moreover, the reaction steps are greatly reduced, the yield can exceed 80%, and the method has certain application value.

Description

technical field [0001] The invention relates to a method for synthesizing a pharmaceutical intermediate iminostilbene, which belongs to the field of pharmaceutical synthesis. Background technique [0002] Iminostilbene (1), iminostilbene, the chemical name is 5H-dibenzo[b,f]azepine, it has high physiological activity, and it has a wide range of functions. First of all, it can prevent and treat hepatitis C by itself. Secondly, as a pharmaceutical intermediate, iminostilbene can be used to synthesize antiepileptic drugs carbamazepine, oxcarbazepine and antidepressant imipramine. Furthermore, iminostilbene can stabilize the anion complex of rhodium catalysts and be used for the synthesis of rhodium catalysts (mainly used as automobile exhaust catalysts). Finally, iminostilbene is also an important synthetic raw material in genetic engineering and materials science, for example, it can be used as a synthetic raw material for porphyrin compounds. At present, the synthesis of im...

Claims

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Application Information

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IPC IPC(8): C07D223/22
Inventor 宋国强唐龙曹引梅吴建华陈鹏魏涛沈梦笔
Owner CHANGZHOU UNIV
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