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Synthesis method of iminostilbene carbonyl chloride

A technology of iminostilbenoyl chloride and iminodibenzoyl chloride, which is applied in the synthesis field of iminostilbenoyl chloride, can solve the problems of low utilization rate of bromine, high equipment requirements, and large equipment investment, so as to improve the utilization rate, Good labor protection and low investment in equipment

Active Publication Date: 2013-05-08
SHANGHAI MODERN HASEN SHANGQIU PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Chinese patent CN200810062839.2 discloses a method for synthesizing iminostilbene in one step by dehydrogenating iminodibenzyl as a raw material under the action of a catalyst. The process has production costs It has the advantages of low cost and short synthesis steps, but its promotion is limited due to its high requirements on equipment, high reaction temperature, harsh operating conditions, expensive catalyst and large equipment investment.
[0006] Chinese patent CN 200410066503.5 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) Liquid bromine is used in the production process, because liquid bromine is a strong irritant substance, which is not conducive to labor protection
[0007]2) Bromine utilization rate is low
[0008]3) The discharge of hydrogen bromide is large during the reaction process, which is not conducive to environmental protection

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  • Synthesis method of iminostilbene carbonyl chloride
  • Synthesis method of iminostilbene carbonyl chloride
  • Synthesis method of iminostilbene carbonyl chloride

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Embodiment 1

[0026] A kind of synthetic method of iminostilbenoyl chloride, it comprises the steps: in reactor, add 300ml chlorobenzene, 106g (0.410mol) iminodibenzoyl chloride, 77g (0.431mol) N-bromosuccinyl Amine and 2g of azobisisobutyronitrile, the oil bath was heated to 120°C for bromination reaction for 20 hours (1g of azobisisobutyronitrile was added every 6h during the reaction process), and then heated to reflux (about 140°C) for 5h To remove hydrogen bromide (until no hydrogen bromide is discharged). After the reflux, the reaction solution was cooled to 1°C, added 300ml of water to wash once, and allowed to stand for stratification. The organic phase was dried with sodium bicarbonate, concentrated under reduced pressure and evaporated to remove chlorobenzene, then added 200ml of ethanol, stirred at room temperature for 1 hour, filtered, and the filter cake Dry below 50°C to obtain about 83g of yellow solid iminostilbenoyl chloride, the yield is about 80%.

Embodiment 2

[0028] A kind of synthetic method of iminostilbenoyl chloride, it comprises the steps: in reactor, add 300ml xylene, 106g (0.410mol) iminodibenzoyl chloride, 67.5g (0.236 mol) dibromohydantoin and 2g dibromide Azobisisobutyronitrile, the temperature of the oil bath was raised to 100°C for bromination reaction for 15 hours (1 g of azobisisobutyronitrile was added every 6 hours during the reaction), and then the temperature was raised to reflux for 4 hours to remove hydrogen bromide. After the reflux, the reaction solution was cooled to 5°C, added 300ml of water to wash once, allowed to stand for stratification, the organic phase was dried with sodium bicarbonate, concentrated under reduced pressure and evaporated to remove xylene, then added 200ml of ethanol, stirred at room temperature for 1 hour, filtered, and the filter cake After drying, about 81 g of yellow solid iminostilbene carboxyl chloride was obtained, and the yield was about 78%.

Embodiment 3

[0030] A kind of synthetic method of iminostilbenoyl chloride, it comprises the steps: add 300ml chlorobenzene, 106g (0.410mol) iminodibenzoyl chloride, 13g (0.086mol) sodium bromate and 4g benzene peroxide in reactor Formyl, the temperature of the oil bath was raised to 110°C, and 28 g (0.175 mol) of bromine was added dropwise to the reactor for bromination reaction for 10 hours, and then the temperature was raised to reflux for 4 hours to remove hydrogen bromide. After the reflux, the reaction solution was cooled to 3°C, added 300ml of water to wash once, allowed to stand for stratification, the organic phase was dried with sodium bicarbonate, concentrated under reduced pressure and evaporated to remove chlorobenzene, then added 200ml of ethanol, stirred at room temperature for 1 hour, filtered, and the filter cake After drying, about 81 g of yellow solid iminostilbene carboxyl chloride was obtained, and the yield was about 78%.

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Abstract

The invention discloses a synthesis method of iminostilbene carbonyl chloride. The synthesis method comprises the following steps of: performing bromination reaction on iminodibenzyl carbonyl chloride and a brominating agent at the temperature of 100-120 DEG C for 10-20 hours under the action of an organic solvent and an initiator, then performing heating reflux for 4-5 hours, and performing post-treatment on a reaction solution after the end of reflux. According to the method disclosed by the invention, by selecting different brominating agents, the utilization rate of the brominating agent is improved, and the requirements for labor protection during the production process are reduced so as to be conducive to environmental protection.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical preparations, and in particular relates to a synthesis method of iminostilbenoyl chloride. Background technique [0002] Iminostilbene carbonyl chloride (Iminostilbene carbonyl chloride) is a pharmaceutical intermediate, which is hydrolyzed to obtain iminostilbene. Iminostilbene carbonyl chloride and iminostilbene are key intermediates for the synthesis of carbamazepine and opipramol. the use of. [0003] the [0004] Iminostilbene carboxyl chloride Carbamazepine Opipramol [0005] Chinese patent CN200810062839.2 discloses a method for synthesizing iminostilbene in one step by dehydrogenating iminodibenzyl as a raw material under the action of a catalyst. This process has the advantages of low production cost and short synthesis steps, but because of its high requirements for equipment , High reaction temperature, harsh operating conditions, expensive catalyst and large equipment i...

Claims

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Application Information

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IPC IPC(8): C07D223/22
Inventor 陈洪王英利刘统斌江正祥唐秋玲宋振峰王紫华
Owner SHANGHAI MODERN HASEN SHANGQIU PHARMA