Methane → 1-(2-Nitro-1-imidazolyl)-3-(2-fluoroethylamino)-2-propanol hydrochloride
Reaction equation
[O:1]1[CH2:12][CH:2]1[CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[C:5]1[N+:9]([O-:11])=[O:10].[N+](C1NC=CN=1)([O-])=O.[Cl-:21].[F:22][CH2:23][CH2:24][NH3+:25].[OH-].[Na+].C.Cl>C(O)C>[ClH:21].[N+:9]([C:5]1[N:4]([CH2:3][CH:2]([OH:1])[CH2:12][NH:25][CH2:24][CH2:23][F:22])[CH:8]=[CH:7][N:6]=1)([O-:11])=[O:10]Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 1-(2,3-epoxypropyl)-2-nitroimidazole prepared by the method described by Beaman et al. [Beaman, A.G., Tautz, W. and Duschinsky, R., 1968; Studies in the Nitroimidazole Series. III, Antimicrobial Agents and Chemotherapy, pp. 520-530] (4.00 g, 23.7 mmol), 2-fluoro-ethylammonium chloride (5.00 g, 50.2 mmol) and sodium hydroxide (2.00 g, 50.0 mmol) in ethanol (60 cm3) was stirred at 15° C. for 30 minutes then heated under reflux for 3 hours. The reaction mixture was then treated with decolourising charcoal (0.5 g), cooled and filtered. Concentration under reduced pressure afforded a pale yellow oil which was dissolved in ethanol (20 cm3) and treated with a small excess of anhydrous ethereal hydrogen chloride to give 1-(2-nitro-1-imidazolyl)-3-(2-fluoroethylamino)-2-propanol hydrochloride in the form of a pale yellow crystalline solid (4.38 g, 68.9%) after recrystallisation from aqueous ethanol, m.p. 178°-179° C. (dec. after drying in vacuo.
Workup
- customprepared by the method
- temperaturethen heated
- temperatureunder reflux for 3 hours
- temperaturecooled
- filtrationfiltered
- concentrationConcentration under reduced pressure
- customafforded a pale yellow oil which
Sources & evidence
- ORD record
- ord-7a5fb70cad7e4749b01cd15758d7333a
- Source dataset
- uspto-grants-1992_03
- Patent number
- US05098921
Reaction notes
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