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Preparation method of nizofenone

A technology of nizophenone and methylimidazole, which is applied in the field of preparation of chemical drugs, can solve the problems of low reaction yield, large steric hindrance of nucleophilic substitution reaction, etc., achieve reduced production cost, mild reaction conditions, and increased yield. rate effect

Inactive Publication Date: 2012-10-10
湖南尔文水电建材有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the method reduces one step than the process of the present invention, the steric hindrance of the nucleophilic substitution reaction in the last step is relatively large, and the reaction yield is very low, and the actual yield is about 10%.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Add 20.2g of 2-bromo(or chloro)-5-nitrobenzoic acid methyl ester and 15.3g of 2-(N,N-diethyl)methylimidazole into tetrahydrofuran in sequence, stir, and slowly add 15g of carbonic acid in batches Potassium, heated to 60°C, the reaction time is 5 hours. After the completion of the reaction, add water and ethyl acetate for extraction, separate layers, collect the organic phase, dry, and concentrate to obtain 28.6g of light yellow solid 2.

[0024] IR (KBr) (cm -1 ): 3485, 3129, 2650, 2276, 1821, 1743, 862, 661.

Embodiment 2

[0026] Dissolve 28.6g of Compound 2 in 300mL of methanol, add 8g of NaOH, then add 50mL of water, and react at room temperature for 6 hours. After the reaction is completed, adjust the pH to 6 with dilute hydrochloric acid, remove methanol under reduced pressure, extract with ethyl acetate, and collect organic phase, dried and concentrated to obtain 24.1 g of compound 3 as a white solid. IR (KBr) (cm -1 ): 3486, 3250, 2648, 2269, 1820, 1741, 860, 659.

Embodiment 3

[0028] Dissolve 24.1g of 3 in 250mL of dichloromethane, add 27g of thionyl chloride, the reaction temperature is 50°C, and the reaction time is 2 hours. After the reaction was completed, dichloromethane and unreacted thionyl chloride were removed under reduced pressure to obtain compound 4. The compound was unstable and was directly used in the next reaction.

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PUM

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Abstract

The invention provides a preparation method of nizofenone. The nizofenone is prepared by taking 2-bromo (or chloro)-5-nitrobenzoate and 2-(N, N-diethyl)methylimidazole as starting materials, substituting, hydrolyzing, acylating and performing Friedel reaction. In the first step of the preparation method, a benzene ring and imidazole ring-containing compound is prepared, so that the subsequent reaction steps are carried out under mild conditions, and the yield is greatly improved, so as to reduce the production cost.

Description

technical field [0001] The invention relates to a preparation method of chemical medicine, in particular to a preparation method of compound nizophenone. Background technique [0002] Nizofenone, English name Nizofenone, chemical name (2-Chlorophenyl)[2-[2-[(diethylamino)methyl]-1H-imidazol-1-yl]-5-nitrophenyl]methanone, CAS: 54533-85- 6. The structural formula is: [0003] . [0004] Nizophenone fumarate, that is, nizophenone fumarate is a new drug for improving brain function. It has the function of survival time, has the effect of improving brain function and reducing the focus of cerebral embolism, and has a weak sedative effect. [0005] At present, there is only one synthetic method of nizophenone disclosed, which is recorded in DE2403416A1, and the process route is as follows: [0006] . [0007] This route uses 2-chloro-5-nitrobenzoic acid as a raw material, and successively undergoes acylation, Fuke and substitution to obtain nizophenone. Although the meth...

Claims

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Application Information

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IPC IPC(8): C07D233/64
Inventor 彭勇
Owner 湖南尔文水电建材有限公司
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