3-[(Z)-(5-nitrofuran-2-yl)methylideneamino]-1,3-oxazolidin-2-one

Base Information

• Chemical Name: 3-[(Z)-(5-nitrofuran-2-yl)methylideneamino]-1,3-oxazolidin-2-one
• CAS No.: 67-45-8
• Molecular Formula: C8H7N3O5
• Molecular Weight: 225.161
• Hs Code.: 29349990
• European Community (EC) Number: 200-653-3
• Nikkaji Number: J1.932A
• Wikipedia: Furazolidone
• Wikidata: Q2467555
• NCI Thesaurus Code: C65783
• RXCUI: 4601
• ChEMBL ID: CHEMBL1572167
• Mol file: 67-45-8.mol

Synonyms:Furazol;Furazolidine;Furazolidone;Furoxone;Nifurazolidone

Chemical Property of 3-[(Z)-(5-nitrofuran-2-yl)methylideneamino]-1,3-oxazolidin-2-one

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 3.59E-05mmHg at 25°C
• Melting Point: 254-256°C (dec.)
• Refractive Index: 1.669
• Boiling Point: 342.6 °C at 760 mmHg
• PKA: -1.98±0.20(Predicted)
• Flash Point: 161 °C
• PSA: 100.86000
• Density: 1.6 g/cm³
• LogP: 1.43500
• Storage Temp.: 0-6°C
• Sensitive.: Light Sensitive
• Solubility.: formic acid: soluble50mg/mL
• Water Solubility.: 极微溶于氯仿、水、乙醇和四氯化碳，1L水中溶40mg该品。稍溶于二甲基甲酰胺。
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 225.03857033
• Heavy Atom Count: 16
• Complexity: 326

Purity/Quality:

99% ^*data from raw suppliers

Furazolidone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,F
• Statements: 62-40-36-20/21/22-11-68
• Safety Statements: 36-22-36/37-16

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Animal Feed Additives
• Canonical SMILES: C1COC(=O)N1N=CC2=CC=C(O2)[N+](=O)[O-]
• Isomeric SMILES: C1COC(=O)N1/N=C\C2=CC=C(O2)[N+](=O)[O-]
• Recent ClinicalTrials: Efficacy of Therapy Based on Fecal Molecular Antimicrobial Susceptibility Tests for Helicobacter Pylori Infection
• Uses: 1. The antibacterial spectrum of furazolidone is similar to that of furazolidone. As an anti-infection drug, it is effective in treating Salmonella, Shigella, Escherichia coli, Proteus, Streptococcus, and Staphylococcus aureus. Bacteria are not easy to develop drug resistance this drug. It also dosen’t have cross-resistance with sulfa class antibiotics. It is mainly used for clinically treatment of dysentery, enteritis, typhoid, paratyphoid and topical treatment of vaginal trichomoniasis. 2. The product is a fungicide which has a broad antibacterial spectrum. As an anti-infective drug, it is effective for treating a variety of Gram-positive and negative bacteria including Escherichia coli, Bacillus anthracis, and Paratyphoid bacilli. It is not only effective in the treatment of dysentery, enteritis, but also being used for treating vaginal infections. In recent years, it has a good efficacy for the treatment of typhoid fever. As an additive for animal drugs and drink, it has unique antibacterial effect on Salmonella, Escherichia coli and Salmonella pullorum and also has certain inhibitory effect on the protozoa (coccidia bacteria, etc.) and have them be less prone to evolve drug resistance. A small amount of furazolidone has been used for other applications (such as water-soluble paint and paper pulp) as fungicides. 3. It is an anti-infective drug used for anti-infection of the intestine. 4. Furazolidone, as a fungicide, has a broad antibacterial spectrum. The most susceptible bacteria are Escherichia coli, Bacillus anthracis, paratyphoid rod, Shigella, and Klebsiella pneumoniae. Salmonella typhi is also sensitive to it. It is mainly used for treating susceptible strains-induced dysentery, enteritis, and cholera. It can also be used for treating typhoid, paratyphoid, giardiasis, and trichomoniasis. Combination with anti-acid drugs can be used for treating Helicobacter pylori-induced gastric inflammation. Properties: yellow powder or crystalline powder, odorless, first tasteless and then become slightly bitter; very slightly soluble in water and ethanol; slightly soluble in chloroform and insoluble in ether, soluble in dimethylformamide and nitromethane. Mp: 255 to 259 °C. Decompose while the dissolution. The minimum inhibitory concentration of furazolidone was assessed to study the nonreplicating persistence of M. tuberculosis in aerobic and anaerobic conditions using luminescence-based low-oxygen-recovery assay. Antiprotozoal; antibacterial
• Description: Furazolidone belongs to the group of nitro furans. This antimicrobal (antibacterial and antiprotozoal) agent is used in veterinary medicine both topically and orally, particularly in animal feed. Reactions have been reported in workers exposed to it by contact with animal feed. Cross reactions with other nitrofuran derivatives are rare.
• Clinical Use: Furazolidone is used in gastrointestinal infections and vaginitis. It is mainly used in developing countries to treat diarrheal diseases of varying etiology, but it is not the drug of choice if a specific pathogen has been identified. Use as a secondline agent in giardiasis and as part of multidrug regimens in Helicobacter infection has been advocated. 3-[(5-Nitrofurylidene)amino]-2-oxazolidinone (Furoxone)occurs as a yellow crystalline powder with a bitter aftertaste.It is insoluble in water or alcohol. Furazolidone hasbactericidal activity against a relatively broad range of intestinalpathogens, including S. aureus, E. coli, Salmonella,Shigella, Proteus spp., Enterobacter, and Vibrio cholerae.It is also active against the protozoan Giardia lamblia. It isrecommended for the oral treatment of bacterial or protozoaldiarrhea caused by susceptible organisms. The usualadult dosage is 100 mg 4 times daily.Only a small fraction of an orally administered dose of furazolidoneis absorbed. Approximately 5% of the oral dose isdetectable in the urine in the form of several metabolites.Some gastrointestinal distress has been reported with its use.Alcohol should be avoided when furazolidone is being usedbecause the drug can inhibit aldehyde dehydrogenase.

Technology Process of 3-[(Z)-(5-nitrofuran-2-yl)methylideneamino]-1,3-oxazolidin-2-one

There total 12 articles about 3-[(Z)-(5-nitrofuran-2-yl)methylideneamino]-1,3-oxazolidin-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(2-imino-oxazolidin-3-yl)-(5-nitro-[2]furfuryliden)-amine (5407-76-1) → furazolidone (67-45-8)

Guidance literature:

With acetic acid; sodium nitrite;

DOI:10.1021/ja01613a075

Reference yield:

5-nitro-furfural-[2-(2-hydroxy-ethyl)-semicarbazone] (405-22-1) → furazolidone (67-45-8)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂; benzene

2: H₂O; aqueous H₂SO₄

With thionyl chloride; sulfuric acid; water; benzene;

DOI:10.1021/ja01613a075

Reference yield:

3-amino-2-oxazolidinone (80-65-9) + 5-nitrofurane-2-carboxaldehyde (698-63-5) → furazolidone (67-45-8)

Guidance literature:

With aqueous acid;

DOI:10.1021/ja01613a074

upstream raw materials:

3-amino-2-oxazolidinone

5-nitrofurane-2-carboxaldehyde

phosgene

2-(2-(propan-2-ylidene)hydrazinyl)ethanol

Downstream raw materials:

N-(5-acetamido-2-furfurylidene)-3-amino-2-oxazolidone

3-(4-cyano-2-oxobutylideneamino)-2-oxazolidone

3-amino-2-oxazolidinone

Refernces

REACTION OF DIBENZOYLFUROXANE WITH PRIMARY ALIPHATIC AMINES AND METHYLHYDRAZINE

10.1007/BF00673331

The study investigates the reactions of 3,4-dibenzoylfuroxane (I) with various primary aliphatic amines and methylhydrazine. The chemicals involved include isopropylamine, tert-butylamine, and methylhydrazine, which react with furoxane I to form complex mixtures of products. The reactions proceed exothermically at room temperature and involve the formation of intermediate benzamidoglyoxime, which then undergoes cyclization or decomposition via a Beckmann rearrangement mechanism. The products obtained include isoxazoles (IIIa and IIIb), benzoic acid amides, a salt of benzoic acid and tert-butylamine (IV), N-tert-butylcyanoformamidoxime (V), and a compound with an empirical formula of C10H10N4O2 (VI), whose structure is not definitively established. The study also notes that when the reactions are carried out in ethanol, ethyl benzoate is additionally isolated. The products are characterized using various spectroscopic techniques, including IR, UV, PMR, and 13C NMR spectroscopy.

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