Method for synthesizing 2-(1-imidazol)ethylamine

A synthesis method and imidazole-based technology are applied in the field of preparation of fine chemicals, and can solve the problems of difficulty in obtaining propionamide, expensive 2-ethyl-2-oxazoline, etc., and achieve mild conditions, high total yield, and convenience. Effects of manipulation and control

Inactive Publication Date: 2009-09-16
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This invention relates to an improved process for making certain chemicals that can be used on food products or other materials like medicine. It achieves this by producing these compounds with more than two different starting substances at once while also improving their stability during production.

Problems solved by technology

The technical problem addressed in this patents relates to improving the efficiency or productivity of chemical synthesis processes for producing certain types of molecules called α-substances from amino acids without having drawbacks associated with existing techniques involving multiple steps and/or starting materials.

Method used

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  • Method for synthesizing 2-(1-imidazol)ethylamine

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Experimental program
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Embodiment 1

[0017] (1), the preparation of intermediate (I): add imidazole (4.1g, 60mmol), TEA (1.0ml, 7.2mmol), methanol (60ml) successively in 150ml there-necked flask, slowly add ethyl acrylate (7.7ml , 72mmol), stirred, reacted at 50°C for 5h, column chromatography (CH 2 Cl 2 :CH 3 OH=40:1) isolated a light yellow liquid compound (9.4g), yield 94.8%.

[0018] 1 HNMR (Cl 3 CD-d 6 )δ: 7.50(s, 1H), 7.04(s, 1H), 6.94(s, 1H), 4.26(t, 2H), 4.13(q, 2H), 2.77(t, 2H), 1.24(t, 3H ).

[0019] (2), the preparation of intermediate (II): 80% hydrazine hydrate (7.5ml, 150mmol), ethanol (30ml), slowly drop the mixture of ethanol (10ml) and intermediate (I) (8.40g, 50mmol), The temperature was not higher than 40°C. After stirring for about 30 minutes, the temperature was raised to reflux for 8 hours. Column chromatography (CH 2 Cl 2 :CH 3 OH=20:3) isolated yellow compound 2 (7.26g), yield 94.3%. 1 HNMR (Cl 3 CD-d 6 )δ: 8.41(s, 1H), 7.52(s, 1H), 7.04(s, 1H), 6.91(s, 1H), 4.32(t, 2H), 3.61(...

example 2

[0022] Intermediate (I) was prepared according to the method of Example 1, using acetonitrile as solvent, and the rest of the operations were the same.

example 3

[0024] Intermediate (I) was prepared according to the method of Example 1, THF was used as solvent, and the rest of the operations were the same.

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Abstract

The invention provides a method for synthesizing 2-(1-imidazol)ethylamine, which uses imidazole and ethyl acrylate as raw material, and includes steps of preparing intermediate (1) ethyl 2-(1-imidazol)propionate from the raw material through Michel addition reaction; preparing intermediate (2) 2-(1-imidazol)propionohydrazide from the intermediate (1) through hydrazinolysis reaction; and obtaining the object product 2-(1-imidazol)ethylamine from the intermediate (2) through Curtius rearrangement reaction. The invention has total yield of 72% by imidazole, stable reaction, mild condition, and convenient operation and control.

Description

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Claims

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Application Information

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Owner HEFEI UNIV OF TECH
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