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Synthetic method of furazolidone metabolite AOZ

A technology of oxazolone and reaction, which is applied in the field of chemical synthesis, can solve the problems of poor recovery rate and low synthesis yield, and achieve the effect of reducing sample loss

Inactive Publication Date: 2020-06-19
INST OF QUALITY STANDARD & TESTING TECH FOR AGRO PROD OF CAAS
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AI Technical Summary

Problems solved by technology

[0003] The current method for synthesizing 3-amino-2-oxazolone (AOZ) has low synthetic yield and poor recovery

Method used

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  • Synthetic method of furazolidone metabolite AOZ
  • Synthetic method of furazolidone metabolite AOZ
  • Synthetic method of furazolidone metabolite AOZ

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Experimental program
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Embodiment 1

[0022] Embodiment 1, synthetic 3-amino-2-oxazolone (AOZ)

[0023]

[0024] Step 1: Place ethylene glycol (5g, 1.0 equivalents) in an ice-water bath, add PBr dropwise 3 (2.6 mL, 0.377 equivalents) for 5 min, then warmed to room temperature, and finally heated to the reflux temperature of ethylene glycol, and reacted for 3 hours. After the reaction was completed, the solvent was distilled to obtain the reaction intermediate product 2-bromoethanol (6.0 g, yield 60%). For the reaction flow chart, see figure 1 .

[0025] Step 2: first dissolve the reaction product 2-bromoethanol (1.0 equivalent, 6.0g) in water, add NaOH (1.1 equivalent, 0.512g), react at 100°C for 3h, then cool down to 70°C and add hydrazine hydrate (3.0 Equivalent, 1.75 g) (after diluting hydrazine hydrate with 5 mL of water) reacted overnight. After the reaction was complete, excess 2-bromoethanol and water were removed by vacuum distillation to obtain intermediate 2-hydrazinoethanol (2.6 g, yield 70%). F...

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Abstract

The invention discloses a preparation method of 3-amino-2-oxazolidinone (AOZ). The method comprises the following steps: 1) carrying out a reaction on ethylene glycol and PBr3 to obtain 2-bromoethanol; 2) carrying out a substitution reaction on 2-bromoethanol and an alkali, then adding hydrazine hydrate into the system, continuously carrying out a ring-opening reaction, and removing excessive 2-bromoethanol and water after the reaction is completed to obtain an intermediate 2-hydrazinoethanol; and 3) in the presence of an alkali, carrying out a reaction on 2-hydrazinoethanol and diethyl carbonate to obtain 3-amino-2-oxazolidinone (AOZ). According to the method, a nitrofuran metabolite AOZ is synthesized by adopting a one-pot method at the rear half part, so that the loss of a separated andpurified sample in the synthesis process is greatly reduced.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a method for synthesizing furazolidone metabolite AOZ. Background technique [0002] Furazolidone (furazolidone) is a hydrazone formed by 5-nitrofurfural and 3-amino-2-oxazolidinedione, commonly known as furazolidone, which belongs to nitrofuran drugs. It is a synthetic spectrum antibacterial drug that began to be used in the late 1940s. It has certain antibacterial and anti-inflammatory effects, and is widely used in the prevention and treatment of livestock and poultry, aquatic animal diseases, sterilization and disinfection of aquatic animal breeding environments, and prevention and treatment of intestinal infections in livestock and poultry. Many studies have proved that furazolidone has strong side effects (Wang Qingwei, Liu Xueying, Li Ping, Cheng Jianfeng. Adverse reactions and prevention of furazolidone [J]. Chinese Journal of Hospital Pharmacy. 2000 (03): 55...

Claims

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Application Information

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IPC IPC(8): C07D263/26
CPCC07D263/26
Inventor 王敏王彤彤全灿周剑杨梦瑞刘权辉
Owner INST OF QUALITY STANDARD & TESTING TECH FOR AGRO PROD OF CAAS
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