4936-47-4

Basic information

• Product Name: Nifuratel
• Synonyms: 5-[(Methylsulfanyl)Methyl]-4-[(E)-[(5-nitrofuran-2-yl)Methylidene]aMino]-1,3-oxazolidin-2-one;3-[(5-Nitro-2-furfurylidene)aMino]-5-[(Methylthio)Methyl]-2-oxazolidinone;5-(MethylMercaptoMethyl)-3-(5-nitro-2-furfurylidenaMino)-2-oxazolidinone;2-Oxazolidinone,5-[(Methylthio)Methyl]-3-[[(5-nitro-2-furanyl)Methylene]aMino]-;MACMIROR;5-[(METHYLTHIO)METHYL]-3-[[(5-NITRO-2-FURANYL)METHYLENE]AMINO-]-2-OXAZO-LIDINONE;5-methylthiomethyl-3-(5-nitrofurfurylideneamino)-2-oxazolidone;NIFURATEL
• CAS NO: 4936-47-4
• Molecular Formula: C₁₀H₁₁N₃O₅S
• Molecular Weight: 285.28
• EINECS: 225-576-2
• Product Categories: API;Intermediates & Fine Chemicals;Pharmaceuticals;APIS
• Mol File: 4936-47-4.mol
• Article Data: 12

Chemical Properties

• Melting Point: 176-178°C
• Boiling Point: 423.6 °C at 760 mmHg
• Flash Point: 210 °C
• Appearance: Yellow solid
• Density: 1.57 g/cm³
• Vapor Pressure: 2.21E-07mmHg at 25°C
• Refractive Index: 1.666
• Storage Temp.: -20°C Freezer
• Solubility: Acetone (Sparingly), DMSO (Slightly)
• PKA: -2.49±0.40(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: Nifuratel(CAS DataBase Reference)
• NIST Chemistry Reference: Nifuratel(4936-47-4)
• EPA Substance Registry System: Nifuratel(4936-47-4)

Safety Data

• Statements: 68
• Safety Statements: 36/37
• Hazardous Substances Data: 4936-47-4(Hazardous Substances Data)

Usage

Description

Nifuratel is a derivative of nitrofuran , it is a broad spectrum antibiotic with broad-spectrum antimicrobial effect, Nystatin is a polyene antifungal,it has strong effects on trichomoniasis, bacteria, Candida albicans , it plays a strong killing role especially in common pathogens for gynecological infections such as gram-positive and gram-negative bacteria, trichomoniasis, mold, chlamydia and mycoplasma.

Chemical Properties

Bright Yellow Powder.It is poorly soluble in water, but readily soluble in dimethylformamide.

Originator

Macmiror,Poli,Italy,1965

Uses

Nifuratel is a drug used as an antibacterial, antifungal, antiprotozoal (Trichomonas). Nifuratel has a broad antibacterial spectrum of action and is effective against Chlamydia trachomatis and Mycoplasma spp. as well as fungal infections from Candida spp.

Brand name

Macmiror (Polichimica Sap, Italy); Magmilor (Polichimica Sap, Italy); Polmiror (Polichimica Sap, Italy); Tydantil (Polichimica Sap, Italy).

Clinical Use

Nifuratel indications include:1.bacterial vaginosis, trichomonas vaginitis, vulvovaginal candidiasis, vaginal mixed infections.2.urinary tract infections.3.gastrointestinal amoebiasis and trichomoniasis Jia.

Synthesis

The synthesis of Nifuratel is as follows:Add 450ml of ethanol, 450ml of water, and 50ml of phosphoric acid into the reaction flask, then add 5-nitrofuraldehyde diacetate 267.5 (1.1mol), reflux for 0.5-1h, and naturally cool to room temperature to obtain a 5-nitrofurfural solution. Under dark conditions, add N-amino-5-methylthiomethyl-2-oxazolidinone dropwise to the 5-nitrofurfural solution, stir and react at room temperature for 2 to 3 hours, stand still for crystallization, filter and filtered cake was washed with absolute ethanol solvent (60ml×3) and dried to obtain crude nifuratel. Under dark conditions, take the crude Nifuratel and add 10 times the volume of glacial acetic acid, heat to boil, add activated carbon, filter while hot, the filtrate is allowed to stand for crystallization and filtration, the filter cake is washed with ethanol (60ml×3), nifuratel pure product (197.7g, yield 99.93%, purity 99.93%).

InChI:InChI=1/C10H11N3O5S/c1-19-6-8-5-12(10(14)18-8)11-4-7-2-3-9(17-7)13(15)16/h2-4,8H,5-6H2,1H3/b11-4-

Synthetic route

5-nitrofurane-2-carboxaldehyde (698-63-5) + 3-amino-5-[(methylthio)methyl]oxazolidin-2-one (25517-72-0) → nifuratel (4936-47-4)

Conditions	Yield
at 15 - 40℃; for 5h; Temperature; Large scale;	96.9%
In ethanol; water at 20℃; Darkness;	197.7 g

Upstream product

• 698-63-5 5-nitrofurane-2-carboxaldehyde 
• 25517-72-0 3-amino-5-[(methylthio)methyl]oxazolidin-2-one 
• 92-55-7 5-nitro-2-furfuraldehyde diacetate 

Relevant articles and documents

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.

A synthetic method of Nifuratel (by machine translation)

The invention discloses a method for synthesizing Nifuratel. The method of the invention is sodium methyl mercaptan, ech in catalyst-tetrabutyl ammonium bromide under the effect of the compound into a sulfur [...] propane, resulting a sulfur [...] propane and hydrazine reflux 1 - 3 hours to be hydrazinolysis, to obtain 3 - methylthio - 2 - hydroxy [...]; and the resulting reaction mixture in sodium methoxide under the action of the cyclization, shall be N - amino - 5 - methylthio methyl - 2 - oxazolidone, the resulting product with the 5 - nitro furfural b ethyl ester in dilute mineral acid conditions condensation, get the yellow powder 5 - [(methylthio) methyl] - 3 - [[ (5 - nitro - 2 - furyl methylene] amino] - 2 - oxazolidone. This invention lies in the use of its primary product with the raw material of the nature of the nature of the difference between the direct chemical combination, without rectification and purification, overcomes the tedious operation in production steps, simplifies the synthesis method, convenient for large-scale industrial production. (by machine translation)

Preparation process of anti-infective drug nifuratel

The invention belongs to the technical field of drug synthesis and in particular relates to a preparation process of an anti-infective drug nifuratel. The preparation process comprises the following steps: taking iodomethane, sodium sulfide and chlorocyclopropane as initial raw materials to obtain epoxy propyl methyl sulfide, carrying out ring-opening reaction with hydrazine hydrate to obtain 3-methylmercapto-2-hydroxyl-propylhydrazine, carrying out a ring-closure reaction to obtain N-amino-5-methylthiomethyl-2-oxazolidinone, hydrolyzing 5-nitro furfural diacetate in the presence of trifluoroacetic acid to obtain 5-nitro-2-furancarboxaldehyde, and performing condensation with N-amino-5-methylthiomethyl-2-oxazolidinone, thereby obtaining the nifuratel. Safe and cheap reagents are selected in the process route, and environment hazards are reduced. Meanwhile, the operating difficulty and reaction after-treatment burdens are reduced, the production safety is ensured, the process is a simple, green and economic process route for preparing the nifuratel, and the obtained product is high in yield, excellent in purity and suitable for large-scale industrial production of the nifuratel.