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Preparation method of 10-methoxy iminostilbene

A technology for methoxyiminostilbene and iminostilbene, which is applied in the field of preparation of 10-methoxyiminostilbene, can solve the problem of low product purity, and achieves the effects of reducing production costs and reducing pollution

Inactive Publication Date: 2012-12-05
CHANGZHOU WATSON FINE CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] The above several methods all have the problem that the product purity is not high, but now due to the improvement of the raw material drug requirements, the quality requirements of the key intermediates are also getting higher and higher, and it is urgent to develop a method for preparing 10-methoxyiminostilbene. method of purity

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0024] Example 1: (1), add 250ml of methanol, 30 grams of iminostilbene carboxyl chloride and 70 grams of iminostilbene carboxyl bromide into a 500 ml glass four-neck flask with mechanical stirring, stir well and gradually heat up to reflux, then drop Add 74.25 grams of sodium methoxide with a concentration of 28% by weight, reflux after the dropwise addition, and after HPLC detects that the reaction is complete, gradually cool to 0-10°C to obtain a solid iminostilbene-5-methyl carboxylate, and filter out the iminostilbene-5-methyl carboxylate solid. Methyl 5-formate solid was washed twice with pure water and then dried to obtain 84 g of methyl iminostilbene-5-formate solid for subsequent use, with a yield of 95.5%;

[0025] (2), in the glass four-neck flask of 500ml with mechanical stirring, add 250ml methanol and the 84 gram iminostilbene-5-methyl carboxylates that make in the step (1), add after dibromohydantoin 52.5 grams again Stir and make the solution temperature be -5~...

example 2

[0028] Example 2: (1), add 250ml methanol, 89.5 grams of iminostilbene carboxyl chloride in a 500ml glass four-necked flask with mechanical stirring, stir evenly and gradually heat up to reflux, then add dropwise 74.25 grams of 28% by weight Sodium methoxide, reflux after the dropwise addition, after the reaction is complete as detected by HPLC, gradually cool to 0-10°C to obtain iminostilbene-5-methyl carboxylate solid, filter out iminostilbene-5-methyl carboxylate solid and wash with pure water After washing twice, dry to obtain 83 grams of iminostilbene-5-methyl carboxylate as a solid for future use, with a yield of 94.4%;

[0029] (2), in the glass four-neck flask of 500ml with mechanical stirring, add 250ml methanol and the 83 gram iminostilbene-5-methyl carboxylates that make in the step (1), add after dibromohydantoin 52.5 grams again Stir and make the solution temperature be -5~5°C, filter out the solid after the HPLC detection is complete, wash with -5~5°C methanol tw...

example 3

[0032]Example 3: (1), add 250ml of methanol and 105 grams of iminostilbene carboxyl bromide in a 500ml glass four-necked flask with mechanical stirring, stir evenly and gradually heat up to reflux, then add dropwise 74.25 grams of 28% by weight sodium methoxide, reflux after the dropwise addition, and after the reaction is complete as detected by HPLC, gradually cool to 0-10°C to obtain iminostilbene-5-methyl carboxylate solid, filter out iminostilbene-5-methyl carboxylate solid and use pure Washed twice with water and then dried to obtain 85.3 g of methyl iminostilbene-5-carboxylate as a solid for subsequent use, with a yield of 97%;

[0033] (2), in the glass four-neck flask of 500ml with mechanical stirring, add 250ml methanol and the 85.3 grams of iminostilbene-5-methyl carboxylate obtained in step (1), and then add 53.5 grams of dibromohydantoin Stir and make the solution temperature be -5~5°C, filter out the solid after the HPLC detection is complete, wash with -5~5°C me...

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Abstract

The invention relates to preparation method of 10-methoxy iminostilbene. The preparation method comprises the steps of adding iminostilbene-5-formyl halide or mixture of iminostilbene-5-formyl halide into methanol; dripping alkali metal alcohol salt solution to obtain iminostilbene-5-methyl formate; adding iminostilbene-5-methyl formate and dibromohydantoin into methanol and then agitating and reacting to obtain 10-methoxy-11-bromo-10,11-dihydroiminostilbene-5-methyl formate; adding triethylamine and 10-methoxy-11-bromo-10,11-dihydroiminostilbene-5-methyl formate into methylbenzene, then agitating and reacting to obtain 10-methoxy iminostilbene-5-methyl formate; adding 10-methoxy iminostilbene-5-methyl formate and alkali metal hydroxide or alkali metal alcoholate into methanol and then agitating and reacting to obtain high-purity 10-methoxy iminostilbene. The preparation method has the advantages that the reaction product is high in purity and refining is not needed.

Description

technical field [0001] The invention relates to a preparation method of 10-methoxyiminostilbene, in particular to a preparation method of 10-methoxyiminostilbene using iminostilbene-5-formyl halide or a mixture thereof as a raw material. Background technique [0002] 10-methoxyiminostilbene, the molecular formula is C15H13NO, the molecular weight is 223.2, and the appearance is bright yellow crystalline solid; its structural formula is: [0003] [0004] It is an important intermediate of anti-epileptic drugs oxcarbazepine and carbamazepine. At present, its synthesis methods mainly include the following methods: [0005] 1. GB943277 describes a synthetic method of 10-methoxyiminostilbene, the route is as follows [0006] [0007] In this method, raw material III reacts with alkali metal hydroxide to obtain II, and then reacts with alkali metal alkanoate to obtain I. The reaction time of the first step needs 14 hours, and the reaction of the second step needs 18 hours,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D223/22
Inventor 孙富强李红功殷瑞东孙克周
Owner CHANGZHOU WATSON FINE CHEM
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