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Method for synthesizing iminostilbene

A technology of iminostilbenes and synthetic methods, applied in the direction of organic chemistry, can solve the problems of heavy pollution, long steps, low yield, etc., and achieve the effect of optimizing reaction conditions and shortening reaction steps

Inactive Publication Date: 2014-01-01
JIANGSU TOHOPE PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] In order to solve the above-mentioned technical problems, i.e. the problems of long steps, heavy pollution and low yield in the synthesis method of iminostilbene in the prior art, the present invention provides a kind of synthetic compound iminostilbene with higher yield, low cost and short steps. easy way

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  • Method for synthesizing iminostilbene
  • Method for synthesizing iminostilbene
  • Method for synthesizing iminostilbene

Examples

Experimental program
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Effect test

Embodiment 1

[0027] Under argon protection, add 0.10g (0.90mmol) of L-proline, 1.66g (12mmol) of potassium carbonate, 0.17g (0.30mmol) of cuprous iodide, and 1.30g (6mmol) of o-iodotoluene into a 100mL four-necked flask ), DMSO 9mL, stirred, heated to 90°C, added dropwise 0.64g (6mmol) of o-toluidine, reacted for 48-96 hours, followed by TLC. After the reaction was completed, cool to room temperature, pour into 14 mL of water, extract with ethyl acetate (3×30 mL), combine the organic layers, wash with saturated brine, dry over anhydrous sodium sulfate, filter, and distill the filtrate under reduced pressure to obtain a brown solid, add Petroleum ether (2 mL) was dissolved, filtered to obtain a yellow solid, and finally recrystallized from toluene to obtain 0.24 g of a golden yellow solid, with a yield of 20.72% and a purity of ≥98%.

Embodiment 2

[0029] Under argon protection, add 0.17g (1.50mmol) of L-proline, 1g (18mmol) of potassium hydroxide, 0.13g (0.90mmol) of cuprous bromide, and 1.54g (9mmol) of o-bromotoluene into a 100mL four-necked flask. ), DMSO 15mL, stirred, heated to 100°C, added o-toluidine 0.64g (6mmol) dropwise, reacted for 48-96 h, followed by TLC. After the reaction was completed, cool to room temperature, pour into 22.50 mL of water, extract with ethyl acetate (3×30 mL), combine the organic layers, wash with saturated brine, dry over anhydrous sodium sulfate, filter, and distill the filtrate under reduced pressure to obtain a brown solid. Add petroleum ether (2 mL) to dissolve, filter to obtain a yellow solid, and finally recrystallize with toluene to obtain 0.28 g of a golden yellow solid, with a yield of 24.17% and a purity of ≥98%.

Embodiment 3

[0031] Under argon protection, add 0.14g (1.20mmol) of L-proline, 0.82g (15mmol) of sodium methoxide, 0.12g (0.60mmol) of cuprous iodide, and 1.57g (7.20mmol) of o-iodotoluene into a 100mL four-neck flask. mmol), DMSO 12mL, stirred, heated to 100°C, 0.64g (6mmol) of o-toluidine was added dropwise, reacted for 48-96 hours, followed by TLC. After the reaction was completed, cool to room temperature, pour into 18mL water, extract with ethyl acetate (3×30mL), combine the organic layers, wash with saturated brine, dry over anhydrous sodium sulfate, filter, and distill the filtrate under reduced pressure to obtain a brown solid, add Petroleum ether (2 mL) was dissolved and filtered to obtain a yellow solid, which was recrystallized from toluene to obtain 0.49 g of a golden yellow solid with a yield of 42.31% and a purity of ≥98%.

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Abstract

The invention discloses a method for synthesizing iminostilbene. The method is characterized in that o-toluidine and o-halotoluene are heated for reacting with each other in an organic solvent in the presence of a catalytic amount of a copper compound and L-proline as well as alkali to prepare a target product, namely iminostilbene. According to the method for synthesizing iminostilbene, disclosed by the invention, o-toluidine reacts with o-halotoluene through a 'one-pot method' to directly obtain iminostilbene, reaction steps are greatly shortened, the reaction can be carried out at a relatively low temperature, and the yield can reach more than 40%, so that the simple method for synthesizing iminostilbene is short in step, relatively high in yield and low in cost.

Description

technical field [0001] The invention belongs to the field of drug synthesis and relates to a method for synthesizing iminostilbene, a key intermediate of carbamazepine. Background technique [0002] Carbamazepine (1), Carbamazepine, whose chemical name is 5H-dibenzo[b,f]azepine-5-carboxamide, was synthesized in 1950, and it is the first-generation drug effective in the treatment of epilepsy. Not only has anti-epileptic effect, but also has anti-peripheral neuralgia, anti-diuretic, anti-manic depression, anti-arrhythmia and other effects. With the rapid growth of central nervous system (CNS) drugs in the pharmaceutical industry and the increasing clinical application of carbamazepine, the consumption of carbamazepine is bound to increase significantly. Therefore, if a low-cost, low-pollution carbamazepine synthesis route can be developed, it will have great social and economic benefits. [0003] At present, there are many patents and literature reports on the synthesis rout...

Claims

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Application Information

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IPC IPC(8): C07D223/22
CPCC07D223/22
Inventor 宋国强唐龙冯筱晴曹引梅邹振荣殷屹峰钱振青周小军
Owner JIANGSU TOHOPE PHARMA
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