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Method for preparing compound of thiazole formaldehyde class

A compound and formaldehyde technology, which is applied in the field of preparation of 2-thiazole formaldehyde compounds, can solve the problems of 2-methylthiazole being difficult to obtain, difficult to industrialize, and three waste pollution, etc., to facilitate industrial operation, reduce requirements and costs, and reduce production cost effect

Active Publication Date: 2007-10-10
ZHEJIANG JIUZHOU PHARM CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] However, these methods are not ideal enough. For example, the raw material in the first method needs to be prepared by 2-methylthiazole, which is not easy to obtain; in the second method, harsh reactions such as high temperature, high pressure, and strong acid are required. conditions, and the pollution of the three wastes is serious; although the third method is cheap and easy to get raw materials, the yield is very low, about 10%; the fourth method needs to be processed at ultra-low temperature ( -75℃) to react, so it is not easy to be industrialized

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Preparation of 2-bromothiazolyl Grignard reagent

[0048] Put 200ml (0.40mol) of bromoethane Grignard reagent / tetrahydrofuran solution with a concentration of 2mol / L into a 500ml four-necked flask, stir, cool in an ice-water bath to 0-5°C, and slowly add 59g (0.36 mol), after about 0.5 hours, the reaction was continued at 0°C for 2 hours. As detected by TLC, the raw material 2-bromothiazole was completely reacted. Take 0.5ml of the reaction solution and place it in a test tube, add 2ml each of ethyl acetate and 0.1N dilute hydrochloric acid, shake, separate layers, take the organic layer for GC analysis, the content of the raw material 2-bromothiazole is less than 1%.

Embodiment 2

[0050] Preparation of 2-thiazolecarbaldehyde

[0051](1) In a 1000ml four-necked flask, put 200mL of toluene, 73g (1.0mol) of N,N dimethylformamide, stir, and cool in a water bath to 5-10°C. Stirring reagent solution, slowly added, after completion, stirred and reacted at 10°C for about 12 hours. In another 1000ml four-necked bottle, put 200ml of 2N hydrochloric acid into it, and control the temperature in a water bath at about 15°C. Slowly add the above reaction solution into it, stir for 0.5 hours, let it stand for stratification, and continue to extract the water layer twice with 200ml of toluene; combine The organic layer was washed with 100ml of water, dried over anhydrous MgSO for 0.5 hours, filtered, and the mother liquor was concentrated to dryness at 70°C under reduced pressure,

[0052] 40.5 g of a light red liquid was obtained. According to GC analysis, the content of 2-thiazole formaldehyde was 86%, and the crude product yield was 99%.

[0053] (2) Take 40.0 g of...

Embodiment 3

[0057] Preparation of 4-ethyl-2-bromothiazole Grignard reagent

[0058] In reaction flask A, put 38.4g (0.20mol) of 4-ethyl-2-bromothiazole and 100ml of diethyl ether, stir, cool to -5~0°C, slowly add bromopropane Grignard agent with a concentration of 2mol / L / 120ml (0.24mol) of ether solution was added in 15 minutes. At about 0°C, the stirring reaction was continued for 3 hours, and the reaction of the raw material 4-ethyl-2-bromothiazole was basically complete as detected by TLC. Take 0.5ml of the reaction solution and put it in a test tube, add 2ml each of ethyl acetate and 0.1N dilute hydrochloric acid, shake, separate layers, take the organic layer for GC analysis, the raw material 4-ethyl-2-bromothiazole is less than 2%.

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Abstract

This invention discloses a method for preparing 2-thiazole formaldehyde compound (chemical formula I). The method comprises: performing halogen-Grignard exchange reaction to 2-bromothiazole compound to obtain a 2-thiazole aromatic Grignard reagent, reacting with formamide compound, and hydrolyzing to obtain high-purity 2-thiazole formaldehyde compound with a high yield. The method has such advantages as mild reaction conditions, high speed, high yield, and easy operation, and is suitable for industrialization.

Description

technical field [0001] The invention belongs to the technical field of chemical industry and relates to the preparation of pharmaceutical products and intermediates thereof, in particular to the preparation method of 2-thiazole formaldehyde compounds. Background technique [0002] 2-thiazole formaldehyde compounds can be used to synthesize compounds containing thiazole heterocyclic functional groups, including pesticides, dyes, pharmaceutical products and their intermediates. [0003] For example, for the synthesis of antiviral drugs (WO-A2-02 / 096359 Merck, WO-A1-2004 / 037818 & WO2006045613 Glaxo), for the preparation of heterocyclic compounds for the treatment of obesity (WO2006019957 Schering Corp.) for antiallergic Drug synthesis (WO9011278 & JP-A2-04264076 Green Cross Corp, WO9714686 AstraPharma), antibiotic synthesis (J of Antibiotics 1988 41-1 134-8 Pfizer Inc.), etc. [0004] Known 2-thiazole formaldehyde compounds can be prepared by the following method: [0005] (1...

Claims

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Application Information

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IPC IPC(8): C07D277/24
Inventor 李昌龙楼科侠徐明东张达
Owner ZHEJIANG JIUZHOU PHARM CO LTD
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