Preparation method of 1-isopropenyl-2-benzimidazolone

A benzimidazolone and isopropenyl technology, which is applied in the field of preparation of main raw material 1-isopropenyl-2-benzimidazolone, can solve the problems of high cost, difficult industrialized production, difficult control and the like, and achieves the production cost The effect of reducing and increasing costs and eliminating potential safety hazards

Inactive Publication Date: 2012-07-18
玛耀生物医药(上海)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In this method, because ethyl acetoacetate is used as a raw material and as a solvent for the reaction, the cost is high; and the reaction time is as long as 5 minutes, which is difficult to control and difficult to industrialized production

Method used

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  • Preparation method of 1-isopropenyl-2-benzimidazolone
  • Preparation method of 1-isopropenyl-2-benzimidazolone
  • Preparation method of 1-isopropenyl-2-benzimidazolone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] In a 1000ml four-necked flask equipped with a distiller, add 480g xylene, 108g o-phenylenediamine, 1.5g methylguanidine, then add 150g ethyl acetoacetate, raise the temperature to 125-135°C, and react at this temperature During 7 hours, part of the mixture of by-product alcohol and water was evaporated, xylene was distilled under reduced pressure, and 650ml of 2% hydrochloric acid was added to the obtained crude product, and it was beaten for 1 to 2 hours at 25°C at room temperature, suction filtered, washed with 400g of water, 60 ~80°C, 150~250mbar drying to constant weight to obtain 148g of the target product 1-isopropenyl-2-benzimidazolone.

[0038] It was tested to be consistent with the standard of 1-isopropenyl-2-benzimidazolone.

[0039] HPLC: 98.76%

[0040] mp: 125-125.5°C, C, 62.5; H, 6.2; N, 14.6, yield: 85%.

Embodiment 2

[0042] In a 1000ml four-neck flask equipped with a distiller, add 450g xylene, 100g o-phenylenediamine, 1.4g methylguanidine, then add 160g ethyl acetoacetate, raise the temperature to 125-135°C, and react at this temperature During 8 hours, part of the mixture of by-product alcohol and water was distilled off, xylene was distilled under reduced pressure, and 600ml of 10% hydrochloric acid was added to the obtained crude product, beaten at 30°C for 1 hour, suction filtered, washed with 600g of water, 60-80°C, After drying at 150-250 mbar, 134.5 g of the target product 1-isopropenyl-2-benzimidazolone was obtained.

[0043] Purity HPLC: 97.23%

[0044] mp: 123.5-125.5°C, C, 62.4; H, 6.3; N, 14.6, yield: 83.5%.

Embodiment 3

[0046] In a 1000ml four-necked flask equipped with a distiller, add 420g xylene, 110g o-phenylenediamine, 1.8g triethylamine, then add 135g ethyl acetoacetate, raise the temperature to 125-135°C, and react at this temperature During 9 hours, part of the mixture of by-product alcohol and water was distilled off, xylene was distilled under reduced pressure, and the obtained crude product was added with 600ml of 5% hydrochloric acid, beaten at room temperature for 1 hour, suction filtered, washed with 600g of water, 60~80℃, 150~ Dry at 250 mbar to constant weight to obtain 142 g of the target product 1-isopropenyl-2-benzimidazolone, mp: 124-125.5°C, C, 62.5; H, 6.3; N, 14.5, yield: 81.5%. Purity HPLC: 97.86%

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Abstract

The invention provides a preparation method of 1-isopropenyl-2-benzimidazolone. The method comprises the following steps of: reacting o-phenylenediamine I and acetacetic ester II serving as raw materials under the action of a catalyst to obtain a 1-isopropenyl-2-benzimidazolone crude product; and adding olefin acid into the crude product, performing suction filtration, washing with water, and drying to obtain a purified 1-isopropenyl-2-benzimidazolone III product. The reaction formula of the product is shown in the specifications. Compared with the prior art, the method has the advantages that: the problems of large potential safety hazard, severe three waste pollution and the like existing in the conventional method are solved fundamentally, the yield is increased by 15-20 percent, and production cost is reduced. A small amount of catalyst is added, so that the reaction yield is increased remarkably without increasing the cost. The method is easy, convenient and safe for operating, is suitable for industrial production, and has great practical application value and social and economic benefits.

Description

technical field [0001] The invention relates to medicinal chemistry, in particular to a preparation method of 1-isopropenyl-2-benzimidazolone, a main raw material for synthesizing zilpaterol. Background technique [0002] Zipaterol is an adrenergic beta-2 agonist with the following structural formula: [0003] [0004] Zipatero [0005] The chemical name of zilpaterol is 4,5,6,7-tetrahydro-7-hydroxy-6-[(1-methyl-ethyl)-imidazo[4,5,1-jk]-[1 ] Benzazepine X-2-(1H)-one. It can be used in medicine to induce sympathetic nerve excitation, selectively excite the β-2 receptors in the respiratory tract, cause relaxation of bronchial smooth muscle, reduce vascular permeability, and play an antiasthmatic effect. It can also selectively excite the β-2 receptors of the myocardium, the conduction system and the sinoatrial node, strengthen the contractility of the myocardium, accelerate conduction, increase the heart rate, and increase the excitability of the myocardium. Therefore, ...

Claims

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Application Information

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IPC IPC(8): C07D235/26
Inventor 陈品岗蔡珍珍
Owner 玛耀生物医药(上海)有限公司
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