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Synthetic method for carbamazepine intermediate iminostilbene carbonyl chloride

A technology of iminostilbenecarbonyl chloride and iminodibenzylcarbonyl chloride is applied in the field of synthesis of pharmaceutical intermediates and can solve the problems of unfavorable labor protection, limited improvement of bromine utilization rate, low bromine utilization rate and the like

Active Publication Date: 2017-03-01
ZHEJIANG HUAZHOU PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Chinese patent CN200410066503.5 discloses a method of reacting iminodibenzoylchloride with bromine and then removing hydrogen bromide at high temperature to obtain iminostilbenoylchloride. The process has the following disadvantages: (1) used in the production process Liquid bromine, because liquid bromine is a strong irritating substance, is not conducive to labor protection
[0009] But Chinese patent 201310029806.9 proposes to use sodium bromate to react with hydrogen bromide produced in bromination to generate elemental bromine to improve the utilization rate of bromine, but this reaction needs to be carried out in the water phase, while hydrogen bromide is in the oil phase Some of the bromine generated in the bromine will be directly discharged, and due to the existence of the water phase, both the bromine in the bromine water in the raw material and the elemental bromine generated will be partially dissolved in the water and cannot react with the iminodibenzoyl chloride, so the bromine limited utilization of

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Embodiment 1

[0026] A synthetic method of carbamazepine intermediate iminostilbenoyl chloride, which comprises the steps of: adding chlorobenzene 848ml, iminodibenzoyl chloride 106g (0.410mol), benzoyl peroxide 4.24g and Benzyltriethylammonium chloride 6.36g, the oil bath is heated to 92°C, sodium bromate 13.6 (0.09mol) is added to the reactor, and bromine 28.8g (0.18mol) is added dropwise at a constant speed, and the dropping time is 4.5 h, then raised the temperature to 97°C and refluxed for 4 hours. After the reflux, the reaction solution was cooled to 20°C, poured into 300ml of methanol solution, allowed to stand for 4 hours, filtered, and the filter cake was dried and concentrated under reduced pressure to remove the organic solvent. Dissolve in 848ml of toluene, add activated carbon for recrystallization and decolorization, filter, the filtrate is cooled to crystallize, filter, and vacuum dry to obtain about 95g of yellow solid iminostilbene carboxylic acid chloride, the yield is 90.5...

Embodiment 2

[0028] A synthetic method of carbamazepine intermediate iminostilbenoyl chloride, which comprises the steps of: adding chlorobenzene 848ml, iminodibenzoyl chloride 106g (0.410mol), benzoyl peroxide 4.24g and Benzyltriethylammonium chloride 5.30g, the oil bath is heated to 92°C, sodium bromate 13.6 (0.09mol) is added to the reactor, and bromine 28.8g (0.18mol) is added dropwise at a constant speed, and the dropping time is 4.5 h, then raised the temperature to 97°C and refluxed for 4 hours. After the reflux, the reaction solution was cooled to 20°C, poured into 300ml of methanol solution, allowed to stand for 4 hours, filtered, and the filter cake was dried and concentrated under reduced pressure to remove the organic solvent. Dissolve in 848ml of toluene, add activated carbon for recrystallization and decolorization, filter, the filtrate is cooled to crystallize, filter, and vacuum dry to obtain about 90g of yellow solid iminostilbene carboxylic acid chloride, the yield is 85.7...

Embodiment 3

[0030] A synthetic method of carbamazepine intermediate iminostilbenoyl chloride, which comprises the steps of: adding chlorobenzene 848ml, iminodibenzoyl chloride 106g (0.410mol), benzoyl peroxide 4.24g and Benzyltriethylammonium chloride 8.48g, the oil bath is heated to 92°C, sodium bromate 13.6 (0.09mol) is added to the reactor, and bromine 28.8g (0.18mol) is added dropwise at a constant speed, and the dropping time is 4.5 h, then raised the temperature to 97°C and refluxed for 4 hours. After the reflux, the reaction solution was cooled to 20°C, poured into 300ml of methanol solution, allowed to stand for 4 hours, filtered, and the filter cake was dried and concentrated under reduced pressure to remove the organic solvent. Dissolve in 848ml of toluene, add activated carbon for recrystallization and decolorization, filter, the filtrate is cooled to crystallize, filter, and vacuum dry to obtain about 94g of yellow solid iminostilbene carboxylic acid chloride, the yield is 89.5...

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Abstract

The invention discloses a synthetic method for a carbamazepine intermediate, i.e., iminostilbene carbonyl chloride. The synthetic method is characterized by comprising the following steps: adding iminodibenzylcarbonyl chloride, chlorobenzene, an initiator and a phase-transfer catalyst, carrying out heating to 90 to 93 DEG C, adding a bromination agent for a reaction, then carrying out heating to 95 to 100 DEG C, carrying out reflux for 4 h at the same time and subjecting a reaction solution obtained after completion of reflux to post-treatment so as to obtain iminostilbene carbonyl chloride. The synthetic method has the beneficial effects that since the phase-transfer catalyst is added, escape of hydrogen bromide is reduced, the utilization rate of bromine is increased, atmospheric pollution is alleviated and production cost is lowered; and the method is suitable for industrial production.

Description

technical field [0001] The present invention relates to a kind of synthetic method of medicine intermediate, more specifically, it relates to a kind of synthetic method of carbamazepine intermediate iminostilbene carboxyl chloride. Background technique [0002] Iminostilbene carboxyl chloride is the main intermediate for the synthesis of carbamazepine. Carbamazepine is used to treat all types of epilepsy except absence seizures, to treat trigeminal neuralgia and to prevent manic depression. [0003] Chinese patent CN200410066503.5 discloses a method of reacting iminodibenzoylchloride with bromine and then removing hydrogen bromide at high temperature to obtain iminostilbenoylchloride. The process has the following disadvantages: (1) used in the production process Liquid bromine, because liquid bromine is a strong irritant, is not conducive to labor protection. (2) Bromine utilization rate is low. As can be seen from the following reaction formula, the reaction generates hy...

Claims

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Application Information

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IPC IPC(8): C07D223/22
CPCC07D223/22Y02A50/20
Inventor 戴朝云徐委岭
Owner ZHEJIANG HUAZHOU PHARMA CO LTD
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