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Synthetic method for imidazo-[1, 2a]-3,8-PET

A technology of ethyl diformate and a synthetic method, applied in the field of organic synthesis, can solve the problems of lack of literature and patent reports, high market price, difficult synthesis and the like, and achieve the effects of stable product quality, easy operation and simple post-processing

Inactive Publication Date: 2015-09-02
SHANDONG YOUBANG BIOCHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This product has great value, its synthesis is difficult, the market price is expensive, lack of literature and related patent reports

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] 600mmol (71.7g) N,N-dimethylformamide dimethyl acetal is both a solvent and a reaction material, and 2-aminonicotinic acid ethyl ester (33.2g, 200mmol) in a ratio of 3:1 at 40°C The reaction was carried out for 5 hours, and the N,N-dimethyl-N'-2-(3-formic acid ethyl-pyridinyl)-formamidine intermediate was obtained after the reaction was completed, and the excess N,N-dimethyl was removed by rotary evaporation Formamide dimethyl acetal, add 120 mL (114 g) N,N-dimethylformamide (DMF), NaHCO 3 (25.2g, 300mmol), add ethyl bromoacetate (50.1g, 300mmol) according to the ratio of 2-aminonicotinic acid ethyl ester to ethyl bromoacetate 1:1.5, react at 50°C for 10 hours, after the reaction is completed, cool to room temperature, Add 600 mL of water and 200 mL of ethyl acetate for extraction, separate the organic phase, extract the water phase with ethyl acetate (3×200 mL), combine the organic phases, wash with water (2×150 mL), and wash with 200 mL of saturated brine , anhydrou...

Embodiment 2

[0018] 600mmol (71.7g) N,N-dimethylformamide dimethyl acetal is both a solvent and a reaction material, and 2-aminonicotinic acid ethyl ester (99.7g, 600mmol) in a ratio of 1:1 at 70°C After reacting for 6 hours, the N,N-dimethyl-N'-2-(3-formic acid ethyl-pyridyl)yl-formamidine intermediate was obtained after the reaction was completed, and the excess N,N-dimethylformamide was removed by rotary evaporation Amide dimethyl acetal, add 120 mL (125 g) dioxane, K 2 CO 3 (20.8g, 150mmol), add ethyl bromoacetate (100.2g, 600mmol) according to the ratio of ethyl 2-aminonicotinate and ethyl bromoacetate (1:1), react at 80°C for 10 hours, after the reaction is completed, cool to room temperature, add Extract with 600 mL of water and 200 mL of ethyl acetate, separate the organic phase, extract the water phase with ethyl acetate (3×200 mL), combine the organic phases, wash with water (2×150 mL), and wash with 200 mL of saturated brine, Dry over anhydrous Na2SO4, filter, and concentrate ...

Embodiment 3

[0020] 600mmol (71.7g) N,N-dimethylformamide dimethyl acetal is both solvent and reaction raw material, and 2-aminonicotinic acid ethyl ester ((16.62g, 100mmol) in a ratio of 6:1 at 60°C The reaction was carried out for 5 hours, and the N,N-dimethyl-N'-2-(3-formic acid ethyl-pyridinyl)-formamidine intermediate was obtained after the reaction was completed, and the excess N,N-dimethyl was removed by rotary evaporation Formamide dimethyl acetal, add 120 mL (103g) toluene, triethylamine (30.3g, 300mmol) add ethyl bromoacetate (50.1g , 300mmol), reacted at 100°C for 8 hours, after the reaction was completed, cooled to room temperature, added 600 mL of water and 200 mL of ethyl acetate for extraction, separated the organic phase, extracted the aqueous phase with ethyl acetate (3×200 mL), combined The organic phase was washed with water (2×150 mL), washed with 200 mL saturated brine, anhydrous Na 2 SO 4 Dry, filter, and concentrate the filtrate to obtain the crude product of ethyl...

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Abstract

The invention relates to the field of organic synthesis, and particularly relates to a synthetic method for imidazo-[1, 2a]-3,8-PET, which comprises the following steps of reacting N, N-dimethylformamide dimethyl acetal with ethyl 2-aminopyridine-3-carboxylate at 40-100 DEG C to obtain a purification-free intermediate. The intermediate and ethyl bromoacetate, in a certain proportion, react with each other at 50-160 DEG C in a certain solvent under the effect of alkali. When the reaction is finished, the obtained product is cooled to the room temperature, extracted in the ethyl acetate solution, washed in water and NaCl saturated solution, dried by anhydrous sodium sulfate, rotated, evaporated and concentrated to obtain an imidazo-[1, 2a]-3,8-PET primary product. The imidazo-[1, 2a]-3,8-PET primary product is recrystallized in a mixed solution of n-hexane and ethyl acetate in the volume ratio of 1:1, and then a pure product can be obtained. The above method is easily available in reaction raw material, reasonable in price, mild in reaction condition, easy to operate, easy to control and simple in post-treatment. Products obtained through the above method are stable in quality and high in purity.

Description

(1) Technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a synthesis method of ethyl imidazo[1,2a]-3,8-dicarboxylate. (2) Background technology [0002] Ethyl imidazo[1,2a]-3,8-dicarboxylate is an important intermediate in organic synthesis, mainly used in pharmaceutical intermediates, organic synthesis, organic solvents, and can also be used in dye production, pesticide production and spices, etc. . This product has great value, but its synthesis is difficult, the market price is expensive, and there is a lack of literature and relevant patent reports. (3) Contents of the invention [0003] The problem to be solved in the present invention is to provide a method for synthesizing ethyl imidazo[1,2a]-3,8-dicarboxylate which is simple and reasonable in process, low in cost, high in product purity and suitable for industrialization. [0004] The present invention is achieved through the following technical solution...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 崔淑芬韩猛来新胜曹惊涛
Owner SHANDONG YOUBANG BIOCHEM TECH
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