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Chemical synthesis method for of 2-amino-butanamide hydrochloride

An aminobutyramide, chemical synthesis technology, applied in chemical instruments and methods, organic chemistry, preparation of carboxylic acid amides, etc., can solve the problems of large environmental pollution of sulfur-containing wastewater, poor absorption effect of sulfur dioxide, etc., and achieve great practical value and social Economic benefits, low production cost and mild reaction conditions

Active Publication Date: 2013-01-16
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method uses thionyl chloride. Although the hydrogen chloride produced by thionyl chloride can be absorbed and discharged by lye, the absorption effect of sulfur dioxide is poor, and the sulfur-containing wastewater has a relatively large environmental pollution.

Method used

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  • Chemical synthesis method for of 2-amino-butanamide hydrochloride
  • Chemical synthesis method for of 2-amino-butanamide hydrochloride
  • Chemical synthesis method for of 2-amino-butanamide hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] The ratio of the amount of feed material to 2-aminobutyric acid: bis(trichloromethyl)carbonate: organic amine is 1: 0.8: 0.2, using tetrahydrofuran as a solvent, and the quality of the solvent is 4 times that of 2-aminobutyric acid, and the organic amine For 1,3-dimethyl-2-imidazolidinone.

[0023] Dissolve 23.76g (80mmol) of bis(trichloromethyl)carbonate in 41g of tetrahydrofuran, and put it into a 250mL constant pressure dropping funnel. In a 250mL three-necked flask equipped with a thermometer, reflux condenser absorption device and mechanical stirring, add 10.3g (100mmol) of 2-aminobutyric acid and 2.28g of 3-dimethyl-2-imidazolidinone ( 20mmol). A solution of bis(trichloromethyl)carbonate was added dropwise to the flask at reflux temperature and reacted for 8 hours. Cooled to room temperature, distilled to obtain a pink oil and recrystallized from petroleum ether to obtain a white solid, namely 11.9 g of 4-ethyl-2,5-oxazolidinedione, with a yield of 92.1% and a p...

Embodiment 2

[0026] The ratio of the amount of feed material to 2-aminobutyric acid: bis(trichloromethyl)carbonate: organic amine is 1: 1.2: 0.01, and ethyl acetate is used as the organic solvent, and its consumption is 20 times the quality of 2-aminobutyric acid , the organic amine is triethylamine.

[0027] The reaction temperature was reflux temperature, and the reaction time was 10 hours. Other operations were the same as in Example 1 to obtain 11.3 g of 4-ethyl-2,5-oxazolidinedione with a yield of 87.6% and a purity of 98.1%.

Embodiment 3

[0029] The ratio of the amount of feed material to 2-aminobutyric acid: bis(trichloromethyl)carbonate: organic amine is 1: 1.5: 0.4, and ethyl acetate is used as the organic solvent, and its consumption is 30 times the quality of 2-aminobutyric acid , the organic amine is pyridine.

[0030] The reaction temperature was reflux temperature, and the reaction time was 8 hours. Other operations were the same as in Example 1 to obtain 11.0 g of 4-ethyl-2,5-oxazolidinedione with a yield of 85.3% and a purity of 98.5%.

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Abstract

The invention discloses a chemical synthesis method for 2-amino-butanamide hydrochloride as shown by a formula (IV), which comprises the following steps: using 2-aminobutyric acid as shown by a formula (I) as a raw material; performing chlorization reaction first between the raw material and bis(trichloromethyl) carbonate as shown by a formula (II) in an organic solvent A at a temperature of between 5 DEG C below zero and 110 DEG C; separating and purifying a reaction solution obtained after a sufficient reaction to obtain 4-ethyl-2,5-oxazolidine dione as shown by a formula (III); and aminating and acidulating the 4-ethyl-2,5-oxazolidine dione to obtain the 2-amino-butanamide hydrochloride as shown by the formula (IV). The bis(trichloromethyl) carbonate used in the method is used as a chloridizing reagent to synthesize the 4-ethyl-2,5-oxazolidine dione. Compared with the prior production process, the method has the advantages of low production cost, high yield, advanced process route,mild reaction condition, simple and safe operation, fewer three wastes, and greater implementation value and social and economic benefits.

Description

(1) Technical field [0001] The invention relates to a chemical synthesis method of 2-aminobutanamide hydrochloride. (2) Background technology [0002] 2-aminobutyramide hydrochloride is an important intermediate of the antiepileptic drug levetiracetam, and there are many patent documents such as WO 2006 / 095362 and US 2007 / 087924 reporting the use of 2-aminobutanamide hydrochloride Synthesis of levetiracetam. Therefore, the synthesis of 2-aminobutanamide hydrochloride is particularly important in the production of levetiracetam. [0003] The main method of chemically synthesizing 2-aminobutyramide hydrochloride has: 1) use butyric acid as starting material, obtain 2-aminobutyramide through bromination, methylation, ammoniation, acidification steps, finally adjust acid to obtain 2 - Aminobutanamide hydrochloride (Fr 2847896, CN 101130504). The method requires four-step reactions, uses bromine as an environmentally unfriendly raw material, and requires high pressure for the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C237/06C07C231/10B01J31/02
Inventor 苏为科谢媛媛李坚军张帆夏建胜周章兴陈德响张敏
Owner ZHEJIANG UNIV OF TECH
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