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Preparation method of tulobuterol

A technology of tulobuterol and chlorophenyl, which is applied in the field of preparing and synthesizing tulobuterol, can solve problems such as potential safety hazards and cumbersome post-processing, and achieve the effects of improving production safety, simplifying process operation, and improving production efficiency

Pending Publication Date: 2020-05-29
SHANDONG DYNE MARINE BIOTECHCAL PHARM HLDG CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] The purpose of the present invention is to solve the deficiencies of the prior art such as potential safety hazards and cumbersome post-processing in the existing method, and provide a method with short reaction steps, simple process, mild reaction conditions, safe and easy-to-obtain raw materials, safe operation, and high yield. Tulobuterol preparation method suitable for industrialized production

Method used

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  • Preparation method of tulobuterol

Examples

Experimental program
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Effect test

Embodiment 1

[0042] Embodiment 1: the synthesis of 1-(2-chlorophenyl)-2-bromoethanol

[0043] In a 500mL round-bottomed flask, dissolve 2-chlorostyrene (13.86g, 100mmol) in a mixed solvent of 200mL acetone and 40mL water, and slowly add dibromohydantoin (15.73g, 55mmol) under stirring at room temperature. The reaction was stirred for 2h. TLC (V 乙酸乙酯 :V 石油醚 =1:10) to detect that the reaction was complete, and after most of the acetone was evaporated under reduced pressure, extracted with dichloromethane, washed with saturated sodium bicarbonate, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 1-(2-chlorophenyl)-2 - Bromoethanol (21.43 g, 91%).

Embodiment 2

[0044] Embodiment 2: Synthesis of 1-(2-chlorophenyl)-2-bromoethanol

[0045] Dissolve 2-chlorostyrene (13.86g, 100mmol) in a mixed solvent of 200mL acetone and 100mL water in a 500mL round bottom flask, slowly add dibromohydantoin (15.73g, 55mmol) under stirring at room temperature, after the addition is complete, continue at room temperature The reaction was stirred for 4h. TLC (V 乙酸乙酯 :V 石油醚 =1:10) to detect that the reaction was complete, and after most of the acetone was evaporated under reduced pressure, extracted with dichloromethane, washed with saturated sodium bicarbonate, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 1-(2-chlorophenyl)-2 - Bromoethanol (19.78 g, 84%).

Embodiment 3

[0046] Embodiment 3: Synthesis of 1-(2-chlorophenyl)-2-bromoethanol

[0047] In a 500mL round-bottomed flask, dissolve 2-chlorostyrene (13.86g, 100mmol) in a mixed solvent of 200mL acetonitrile and 40mL water, and slowly add dibromohydantoin (15.73g, 55mmol) under stirring at room temperature. The reaction was stirred for 2h. TLC (V 乙酸乙酯 :V 石油醚 =1:10) to detect that the reaction was complete, after most of the acetonitrile was distilled off under reduced pressure, extracted with dichloromethane, washed with saturated sodium bicarbonate, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 1-(2-chlorophenyl)-2 - Bromoethanol (21.20 g, 90%).

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Abstract

The invention provides a preparation method of tulobuterol. The technical problems of potential safety hazard, complicated post-treatment and the like in the existing method are solved. According to the method, a compound 1-(2-chlorphenyl)-2-tert-butylaminoethanol is synthesized from industrially available 2-chlorostyrene through a two-step reaction. The method is short in reaction step, mild in reaction condition, simple and convenient to operate, high in yield and good in application and development prospect, and can be used for preparing tulobuterol.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a new method for preparing and synthesizing tulobuterol using 2-chlorostyrene as a raw material. Background technique [0002] Tulobuterol (tulobuterol), a selective beta 2 Receptor agonist was approved as an anti-asthma drug in Japan in 1981. It was used in the treatment of asthma and chronic obstructive disease (COPD) in 1998. Currently, it is mostly used as a patch to treat children. The indications are to relieve bronchial cough, acute bronchitis, chronic bronchitis, emphysema and other airways. Symptoms such as dyspnea caused by obstructive disease. Tulobuterol, whose chemical name is 1-(2-chlorophenyl)-2-tert-butylaminoethanol, has the following chemical structure: [0003] [0004] The original synthetic route of tulobuterol is as follows: 2-chloroacetophenone is used as the starting material, and the target compound is obtained through three-step reaction of bromoc...

Claims

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Application Information

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IPC IPC(8): C07C213/08C07C215/30
CPCC07C213/08C07C29/03C07C215/30C07C33/46
Inventor 颜世强何淑旺吴晓东景亚军
Owner SHANDONG DYNE MARINE BIOTECHCAL PHARM HLDG CO LTD
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