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Furaltadone

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Furaltadone Basic information
Furaltadone Chemical Properties
  • Melting point:206°C (dec.)
  • Boiling point:462.63°C (rough estimate)
  • Density 1.3046 (rough estimate)
  • refractive index 1.6120 (estimate)
  • storage temp. Sealed in dry,2-8°C
  • pkapKa 5.0 (Uncertain)
  • form neat
  • BRN 8130725
  • EPA Substance Registry SystemFuraltadone (139-91-3)
Safety Information
  • Hazard Codes Xn,Xi
  • Risk Statements 22-36/37/38
  • Safety Statements 3-26
  • RIDADR 3249
  • WGK Germany 3
  • RTECS RQ3620000
  • HazardClass 6.1(b)
  • PackingGroup III
MSDS
Furaltadone Usage And Synthesis
  • DescriptionThis nitrofuran derivative can be added to animal feed. It induced contact dermatitis in a farm employee.
  • Chemical PropertiesYellow Crystalline Solid
  • OriginatorAltafur,Norwich Eaton,US,1959
  • UsesA metabolite of Nitrofuran in milk. Antibacterial
  • DefinitionChEBI: An oxazolidinone that is 1,3-oxazolidin-2-one substituted at position 1 by a (5-nitro-2-furyl)methylene]amino group and at position 5 by a morpholin-4-ylmethyl group. An antibacterial formerly used oraly but withdrawn due to toxicity, it is used topically as the hydrochloride salt) for treatment of ear disorders.
  • Manufacturing Process11.17 g (0.78 mol) 3-(N-morpholinyl)-1,2-epoxypropane, BP 76.5°C to 78°C. 3.9 mm, prepared by Eisleb's method for 3-(1-piperidyl)-1,2-epoxypropane (US Patent 1,790,042) is added dropwise in 12 minutes to 19.5 g (0.39 mol) 100% hydrazine hydrate, which has been warmed to 85% on the steam bath, and is being mechanically stirred. The heat of the reaction maintains the internal temperature at 90°C to 100°C without further external heating. The reaction mixture is then warmed on the steam bath for an additional two hours (90°C to 95°C). The excess hydrazine hydrate is removed in vacuo. The residue of viscous 1-hydrazino-3-morpholinyl-2-propanol is not distilled, but is mixed with 10.16 g (0.086 mol) diethyl carbonate and a solution of 0.3 g sodium metal in 15 ml methyl alcohol. The mixture is refluxed about 2 hours under a 15 cm Widmer column, the alcohol being removed leaving a thick, green liquid residue, which is cooled and the precipitate which forms is removed by filtration and washed well with ether. Yield 82%. MP 114°C to 116°C. Recrystallization from isopropanol gives purified 3-amino-5-(Nmorpholinyl)-methyl-2-oxazolidone, MP 120°C as the intermediate.
    It is not necessary that the intermediate be separated from the reaction medium in the preparation of the end product. Instead, the reaction mixture, after cooling, is treated with 200 ml of water acidified with 42 ml 10% hydrochloric acid solution, and filtered. To the clear, light yellow filtrate is added dropwise a solution of 9.8 g (0.07 mol) 5-nitro-2-furaldehyde in 100 ml ethyl alcohol. An orange solution of the hydrochloride results. The free base is precipitated as yellow plates by making the solution basic with saturated sodium carbonate solution. 14 g of the compound is filtered off by suction, washed with alcohol, and dried. The yield, MP 204°C to 205°C (dec.), is 53% of theoretical based on 3-(N-morpholinyl)-1,2-epoxy-propane.
    Recrystallization from 95% alcohol (75%recovery) raises the melting point to 206°C (dec.).
    The hydrochloride salt is isolated quantitatively by suspending the base in alcohol and adding sufficient aqueous concentrated HCl solution. The precipitate becomes pale yellow, is filtered off, and recrystallized from 80% alcohol. The MP range is about 223°C to 228°C (dec.).
  • Therapeutic FunctionAntibacterial
  • Contact allergensThis nitrofuran derivative can be added in animal feed or in eardrops
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