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Method for synthesizing nitrofuran metabolite furazolidone AOZ-D4

A technology of AOZ-D4 and furazolidone, which is applied in the fields of organic chemistry and organic chemistry, can solve the problems that there are no literatures and patents on the synthesis of furazolidone, and achieve the effect of cheap synthetic raw materials, high yield and short synthesis cycle

Active Publication Date: 2019-04-30
INST OF QUALITY STANDARD & TESTING TECH FOR AGRO PROD OF CAAS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there are no synthetic literatures and patents related to furazolidone AOZ-D4

Method used

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  • Method for synthesizing nitrofuran metabolite furazolidone AOZ-D4
  • Method for synthesizing nitrofuran metabolite furazolidone AOZ-D4
  • Method for synthesizing nitrofuran metabolite furazolidone AOZ-D4

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Embodiment 1

[0041] Embodiment 1, Furazolidone AOZ-D4

[0042] Step 1: Synthesis of Deuterobromoacetic Acid

[0043] Add 3.7ml TFAA (trifluoroacetic anhydride, 46.8mmol) to 1.0mL CH3COOH-D4, add 0.85mL bromine (17.2mmol), react at room temperature for 16h, after the reaction, add deuterium water to quench, reduce pressure Evaporate to dryness to obtain deuterobromoacetic acid.

[0044] The second step: synthesis of deuterated benzyl acetate

[0045] Mix 1.0mL deuterobromoacetic acid (15.6mmol), 15.6mL oxalyl chloride (31.2mmol, 2.0M) and 0.01ml DMF (trace amount), react at 60°C for 3h, then add 4.86ml benzyl alcohol (46.8mmol), Reaction at room temperature for 16h, with D 2 O quenching affords benzyl deuterated acetate.

[0046] The third step: Synthesis of deuterated bromoethanol

[0047] 1.2g NaBD 4 (31.2mmol) was dissolved in 40mL THF, deuterated benzyl acetate (15.6mmol) was added dropwise to the reaction solution, reacted at room temperature for 6h, and evaporated to dryness und...

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Abstract

The invention discloses a furazolidone AOZ-D4 synthesis method, which comprises: 1) carrying out a reaction on deuterated acetic acid and bromine in the presence of TFAA to obtain deuterated bromoacetic acid; 2) carrying out a reaction on the deuterated bromoacetic acid and oxalyl chloride (or SOCl2) in DMF, adding benzyl alcohol, and continuously carrying out a reaction to obtain deuterated benzyl bromoacetate; 3) adding the deuterated benzyl bromoacetate into the THF solution of NaBD4, and carrying out a reaction to obtain deuterated bromoethanol; 4) dissolving hydrazine hydrate in dehydrated alcohol, adding NaOH, stirring, adding the deuterated bromoethanol, and carrying out a reaction to obtain deuterated 2-hydroxyethyl hydrazine; and 5) carrying out a reaction on the deuterated 2-hydroxyethyl hydrazine and dimethyl carbonate in the presence of an alkali to synthesize furazolidone AOZ-D4.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a synthesis method of nitrofuran metabolite-furazolidone AOZ-D4. 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. 200...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/26
CPCC07B2200/05C07D263/26
Inventor 王彤彤王敏周剑常白杨杨梦瑞王冉龚兰
Owner INST OF QUALITY STANDARD & TESTING TECH FOR AGRO PROD OF CAAS
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