25517-72-0

Basic information

• Product Name: 3-amino-5-[(methylthio)methyl]oxazolidin-2-one
• Synonyms: 3-amino-5-[(methylthio)methyl]oxazolidin-2-one;Nifuratel Impurity 8;Nifuratel impurity D
• CAS NO: 25517-72-0
• Molecular Formula: C5H10N2O2S
• Molecular Weight: 162.2101
• EINECS: 247-064-8
• Mol File: 25517-72-0.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 265.7°C at 760 mmHg
• Flash Point: 114.5°C
• Appearance: /
• Density: 1.282g/cm³
• Vapor Pressure: 0.00903mmHg at 25°C
• Refractive Index: 1.545
• PKA: 3.06±0.40(Predicted)
• CAS DataBase Reference: 3-amino-5-[(methylthio)methyl]oxazolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-amino-5-[(methylthio)methyl]oxazolidin-2-one(25517-72-0)
• EPA Substance Registry System: 3-amino-5-[(methylthio)methyl]oxazolidin-2-one(25517-72-0)

Safety Data

• Hazardous Substances Data: 25517-72-0(Hazardous Substances Data)

Usage

General Description

3-amino-5-[(methylthio)methyl]oxazolidin-2-one is a chemical compound with the formula C5H10N2OS. It is an oxazolidine derivative, containing an amino group and a methylthio group. 3-amino-5-[(methylthio)methyl]oxazolidin-2-one is commonly used in pharmaceutical research and drug development, due to its potential biological activities. It has been studied for its antibacterial and antifungal properties, and has shown potential as a promising agent in the development of new antibiotics. Additionally, the compound has been investigated for its potential use in the treatment of various diseases, including cancer and neurological disorders. Further research and studies are ongoing to explore the potential therapeutic applications of 3-amino-5-[(methylthio)methyl]oxazolidin-2-one.

InChI:InChI=1/C5H10N2O2S/c1-10-3-4-2-7(6)5(8)9-4/h4H,2-3,6H2,1H3

Upstream product

• 14359-97-8 3-methylthio-2-hydroxy-propyl hydrazine 
• 616-38-6 carbonic acid dimethyl ester 
• 144-55-8 sodium hydrogencarbonate 
• 105-58-8 Diethyl carbonate 

Downstream Products

• 4936-47-4 Magmilor 
• 4936-47-4 nifuratel 

Relevant articles and documents

Preparation method of nifuratel

The invention relates to a preparation method of nifuratel. The method comprises the following steps: (1) reacting a compound 1 (with the chemical name of epichlorohydrin) with a compound 10 (with thechemical name of tert-butyl hydrazinoformate) to obtain an intermediate 11, (2) reacting the intermediate 11 with CDI (with the chemical name of carbonyl diimidazole) to obtain an intermediate 12, (3) carrying out substitution reaction on the compound 12 and sodium methyl mercaptide to obtain an intermediate 13, (4) under the action of acid, removing Boc groups in the structure of the intermediate 13 are removed, so that an intermediate 4 is obtained, and (5) reacting the intermediate 4 with 5-nitrofurfural to obtain nifuratel. The process route provided by the invention has the advantages ofshort route, cheap and easily available raw materials, simplicity and convenience in operation, high reaction yield, avoidance of production of low-boiling-point sulfur-containing intermediates, environmental friendliness and easiness in industrial production.

Industrial preparation method of nifuratel

The invention provides a preparation method of nifuratel. The preparation method comprises the following steps: (1) reacting sodium methyl mercaptide with epoxy chloropropane to prepare 2-(methylthiomethyl)-oxetane; (2) dropwise adding the 2-(methylthiomethyl)-oxygen heterocyclic propane into hydrazine hydrate, so as to prepare 3-methylthio-2-hydroxyl-propyl hydrazine; (3) adding diethyl carbonate into the 3-(methylthio-2-hydroxy)-propyl hydrazine, so as to prepare N-amino-5-(methylthiomethyl)-2-oxazolidinone; and (4) hydrolyzing the 5-nitrofuran formaldehyde diacetate in the presence of dilute acid to obtain a 5-nitrofurfural solution; under a dark condition, adding the prepared N-amino-5-methylthiomethyl-2-oxazolidinone into a 5-nitrofurfural solution, reacting at room temperature to obtain a nifuratel crude product, and recrystallizing and purifying to obtain a nifuratel pure product.

Process for removing nifuratel cyclization impurities

The invention relates to nifuratel, in particular to a process for removing nifuratel cyclization impurities. The process for removing the nifuratel cyclization impurities comprises the step of preparing a hydrazinolysis product, namely 3-methyl thio-2-hydroxyl-propyl hydrazine and is characterized in that the 3-methyl thio-2-hydroxyl-propyl hydrazine, diethyl carbonate and sodium methoxide are mixed, then cyclized and filtered to obtain cyclization mother liquor, and the cyclization mother liquor is subjected to adsorption treatment through a macro-porous resin packing column, then is condensed with 5-nitro furfural and is re-crystallized to obtain nifuratel. The process provided by the invention has the beneficial effects that through performing treatment on the cyclization mother liquorthrough the macro-porous resin packing column, a cyclized product is completely separated from cyclized impurities and other impurities. The invention overcomes the defect that an existing process cannot completely remove the cyclized impurities and the other impurities and finds a simple, effective, safe and environment-friendly method suitable for industrialization.