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Preparation method of 2-(2-bromo-1,3-thiazol-5-yl) acetonitrile

A technology of bromothiazole and thiazole, which is applied in the field of preparation of 2-acetonitrile, achieves the effects of mild reaction conditions, safe and simple preparation process and purification steps, and convenient industrial production

Inactive Publication Date: 2019-11-22
上海睿升化工科技有限公司
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Problems solved by technology

Thiazole compounds are widely used in the field of medicine. The preparation method of a kind of 2-(2-bromo-1,3-thiazol-5-yl)acetonitrile of the present invention has not been reported in domestic and foreign literature at present, and fills the domestic There is no blank for this product synthesis

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  • Preparation method of 2-(2-bromo-1,3-thiazol-5-yl) acetonitrile

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] (1), preparation of 2-bromothiazole-5-methanol:

[0024] Add methanol (50mL) 2-bromothiazole-5-methyl carboxylate (8.88g, 40mmol, 1.0eq) into a 100mL three-pin bottle, cool to 0°C, add sodium borohydride (2.88g, 80mmol, 2.0eq ), after the system was mixed uniformly, reacted at room temperature for 2h, TLC tracked the end of the reaction, concentrated the reaction solution, added 50mL water, and extracted three times with ethyl acetate (50mL X 3), combined the organic phases, dried over anhydrous sodium sulfate, concentrated, column Chromatographic separation gave 3.52 g of 2-bromothiazole-5-methanol, with a yield of 45%.

[0025] (2), utilizing the 2-bromothiazole-5-methanol obtained in step (1) to prepare 2-bromo-5-bromomethyl-thiazole:

[0026] Add dichloromethane (50mL), 2-bromothiazole-5-carboxylic acid methanol (3.88g, 20mmol, 1.0eq) in sequence in a 100mL three-pin bottle, cool to 0°C, add phosphorus tribromide (16.2g, 60mmol, 3.0eq), after the system was mixed ...

Embodiment 2

[0031] (1), preparation of 2-bromothiazole-5-methanol:

[0032] Add tetrahydrofuran (30mL), methyl 2-bromothiazole-5-carboxylate (4.4g, 20mmol, 1.0eq) into a 100mL three-pin bottle, cool to 0°C, and add sodium borohydride (1.4g, 40mmol, 2.0 eq), after the system was uniformly mixed, reacted at room temperature for 5 hours, TLC tracked the end of the reaction, concentrated the reaction solution, added 50 mL of water and extracted three times with ethyl acetate (50 mL × 3), combined the organic phases, dried over anhydrous sodium sulfate, concentrated, Column chromatography separated to obtain 3.1 g of 2-bromothiazole-5-methanol with a yield of 40%.

[0033] (2), utilizing the 2-bromothiazole-5-methanol obtained in step (1) to prepare 2-bromo-5-bromomethyl-thiazole:

[0034] Add dichloromethane (50mL), 2-bromothiazole-5-carboxylic acid methanol (3.88g, 20mmol, 1.0eq) in sequence in a 100mL three-pin bottle, cool to 0°C, add phosphorus tribromide (16.2g, 60mmol, 3.0eq), after t...

Embodiment 3

[0039] (1), preparation of 2-bromothiazole-5-methanol:

[0040] Add methanol / H 2 O (1:1, 50mL), methyl 2-bromothiazole-5-carboxylate (8.88g, 40mmol, 1.0eq), cooled to 0°C, added sodium borohydride (2.88g, 80mmol, 2.0eq) in portions, After the system was uniformly mixed, reacted at room temperature for 2 hours, TLC followed the completion of the reaction, concentrated the reaction solution, added 100 mL of water and extracted three times with ethyl acetate (50 mL×3), combined the organic phases, dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography 3.4 g of 2-bromothiazole-5-methanol was obtained with a yield of 43%.

[0041] (2), utilizing the 2-bromothiazole-5-methanol obtained in step (1) to prepare 2-bromo-5-bromomethyl-thiazole:

[0042]Add tetrahydrofuran (50mL), 2-bromothiazole-5-carboxylic acid methanol (3.88g, 20mmol, 1.0eq) successively into a 100mL three-pin bottle, cool to 0°C, add phosphorus oxybromide (17.2g, 60mmol, 3.0eq ),...

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Abstract

The invention discloses a preparation method of 2-(2-bromo-1,3-thiazol-5-yl) acetonitrile, which comprises the following steps: S1) adding a first organic solvent and methyl 2-bromothiazole-4-carboxylate into a reaction flask, cooling the mixture to 0 DEG C, adding sodium borohydride, reacting the mixture at room temperature, performing concentration and extraction, combining organic phases, and performing concentration and column chromatography separation to obtain 2-bromothiazole-5-methanol; S2) adding a second organic solvent and the 2-bromothiazole-5-methanol into a reaction bottle, cooling the mixture to 0 DEG C, adding phosphorus tribromide, washing a product with mother liquor, and performing concentration to obtain 2-bromo-5-bromomethyl-thiazole; S3) adding acetonitrile, the 2-bromo-5-bromomethyl-thiazole, potassium carbonate, tetrabutylammonium fluoride and TMSCN sequentially into a reaction flask, performing extraction, combining organic phases, and performing concentration and recrystallization to obtain the 2-(2-bromo-1,3-thiazol-5-yl) acetonitrile. The preparation method breaks through the blank at home and abroad, the preparation process and purification steps are safe and simple, and the preparation method is suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of compound synthesis, in particular to a preparation method of 2-(2-bromo-1,3-thiazol-5-yl)acetonitrile. Background technique [0002] Thiazole compounds widely exist in various foods. Since the discovery of the first thiazole compound in the 1960s, its special structure has made thiazole compounds occupy an important position in many fields such as pesticides, pharmacy, biology and material science, so thiazole products have a very wide range of applications. development value. Thiazole compounds are widely used in the field of medicine. The preparation method of a kind of 2-(2-bromo-1,3-thiazol-5-yl)acetonitrile of the present invention has not been reported in domestic and foreign documents at present, and fills the domestic There is no blank for the synthesis of this product. Contents of the invention [0003] Purpose of the present invention is exactly for the defect existing in the existing ethyl...

Claims

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Application Information

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IPC IPC(8): C07D277/32
CPCC07D277/32
Inventor 李小军檀华东
Owner 上海睿升化工科技有限公司
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