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Synthesis method of 5- methylmorpholine-3-amino-2-oxazolidinyl ketone

A technology of oxazolidinone and methyl morpholine is applied in the field of veterinary drug synthesis and achieves the effects of high yield, good purity and easy availability

Inactive Publication Date: 2013-12-04
HUAZHONG AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But the synthesis report of 5-methylmorpholine-3-amino-2-oxazolidinone has not been reported in the literature yet

Method used

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  • Synthesis method of 5- methylmorpholine-3-amino-2-oxazolidinyl ketone

Examples

Experimental program
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Effect test

Embodiment 15

[0025] Implementation example 15-methylmorpholine-3-amino-2-oxazolidinone preparation

[0026] (1) Add 14.3g morpholino propylene oxide and 20g80% hydrazine hydrate to a 100mL round bottom flask, stir and react at 60°C for 4 hours, then distill under reduced pressure (according to conventional methods) to remove water and excess hydrazine hydrate Hydrazine, in 1-hydrazino-3-morpholine-2-propanol.

[0027] (2) Dissolve 17.5g of 1-hydrazino-3-morpholine-2-propanol in 100ml of anhydrous methanol, add 20ml of dimethyl carbonate, add 8.0g of sodium methylate half an hour later, heat to reflux for 4 hours, After the reaction was completed, methanol was distilled off under reduced pressure (according to a conventional method), and 50 mL of ethanol was added to dissolve and then freeze at -20° C. to separate out 12 g of crystalline 5-methylmorpholine-3-amino-2-oxazolidinone (yield 60%,), the melting point is 116.3°C-118.5°C (the existing literature is 115-120°C).

Embodiment 25

[0028] Preparation of Example 25-methylmorpholine-3-amino-2-oxazolidinone

[0029] (1) Add 14.3g morpholino propylene oxide and 15g80% hydrazine hydrate to a 100mL round bottom flask, stir and react at 60°C for 6 hours, then distill under reduced pressure (according to conventional methods) to remove water and excess hydrazine hydrate Hydrazine to get 1-hydrazino-3-morpholine-2-propanol;

[0030] (2) Dissolve 17.5g of 1-hydrazino-3-morpholine-2-propanol in 100ml of absolute ethanol, add 20ml of ethyl chloroformate, add 8.0g of sodium ethoxide half an hour later, heat to reflux for 2 hours, After the reaction was completed, the ethanol was evaporated under reduced pressure (according to a conventional method), and 50 mL of ethanol was added to dissolve and then freeze at -20° C. to separate out 10 g of crystalline 5-methylmorpholine-3-amino-2-oxazolidinone (yield 50%), melting point 115.5°C-118.3°C (existing literature is 115-120°C).

Embodiment 35

[0031] Preparation of Example 35-methylmorpholine-3-amino-2-oxazolidinone

[0032] (1) Add 29g morpholino propylene oxide and 40g80% hydrazine hydrate to a 100mL round bottom flask, stir and react at 60°C for 8 hours, then distill under reduced pressure (according to conventional methods) to remove water and excess hydrazine hydrate , in 1-hydrazino-3-morpholine-2-propanol.

[0033] (2) Dissolve 35g of 1-hydrazino-3-morpholine-2-propanol in 200ml of isopropanol, add 40ml of ethyl chloroformate, add 15.0g of sodium ethylate half an hour later, heat to reflux for 8 hours, and react At the end, the isopropanol was distilled off under reduced pressure (according to the conventional method), and 80 mL of ethanol was added to dissolve it and freeze at -20°C to precipitate 13 g of crystalline 5-methylmorpholine-3-amino-2-oxazolidinone (produced rate 65%), melting point 117.5°C-120.3°C (existing literature is 115-120°C).

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Abstract

The invention belongs to the field of veterinary drug residue analysis, and particularly relates to a novel chemical synthesis method of 5- methylmorpholine-3-amino-2-oxazolidinyl ketone, which is used in veterinary drug residue analysis and is a marker for furaltadone residue. The synthesis method is characterized in that hydrazine hydrate and morpholine epoxy propane are used as raw materials and react with each other under alkali condition to generate intermediate 1-diazanyl-3-morpholine-propanol; the product then reacts with substituted formate under alkali condition to generate the end product 5- methylmorpholine-3-amino-2-oxazolidinyl ketone. The invention provides for the first time the complete synthesis method of 5- methylmorpholine-3-amino-2-oxazolidinyl ketone (AMOZ), the synthesis procedure is simple and operational, and the reaction condition is mild.

Description

technical field [0001] The invention belongs to the technical field of veterinary drug synthesis, and in particular relates to a chemical synthesis method of 5-methylmorpholine-3-amino-2-oxazolidinone, a residue marker of the banned veterinary drug furaltadone, so that the substance can be used in animals. It provides reference substances for qualitative and quantitative analysis in the detection of residues in non-toxic foods. technical background [0002] Nitrofuran drugs are important antimicrobial drugs, mainly including nitrofuran, nitrofurantoin, furaltadone and furazolidone, etc., which have certain antibacterial effects on Gram-positive bacteria and Gram-negative bacteria, including Salmonella spp. Helicobacter, Escherichia coli, Klebsiella pneumoniae, Enterobacter, Staphylococcus aureus, Enterococcus faecalis, Streptococcus pyogenes, Vibrio cholerae, Campylobacter, Bacteroides, etc. Insects and Giardia also have inhibitory effect. It is mainly used for bacillary d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/26
Inventor 袁宗辉潘源虎周波陶燕飞陈冬梅黄玲利王玉莲谢书宇王旭彭大鹏
Owner HUAZHONG AGRI UNIV
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