Methane → 1-(2-Nitro-1-imidazolyl)-3-(3-bromopropylamino)-2-propanol hydrobromide
Reaction equation
[Br-].[Br:2][CH2:3][CH2:4][CH2:5][NH3+:6].[OH-].[Na+].[O:9]1[CH2:20][CH:10]1[CH2:11][N:12]1[CH:16]=[CH:15][N:14]=[C:13]1[N+:17]([O-:19])=[O:18].C>C(O)C.C(OCC)C>[BrH:2].[N+:17]([C:13]1[N:12]([CH2:11][CH:10]([OH:9])[CH2:20][NH:6][CH2:5][CH2:4][CH2:3][Br:2])[CH:16]=[CH:15][N:14]=1)([O-:19])=[O:18]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 20 °C
Procedure
A solution containing 3-bromopropylammonium bromide (6.47 g, 29.6 mmol) and sodium hydroxide (1.18 g, 29.5 mmol) in ethanol (40 cm3) was stirred at 20° C.; after 1 hour, diethyl ether (40 cm3) was added and the mixture filtered. 1-(2,3-epoxypropyl)-2-nitroimidazole (5.00 g, 29.6 mmol) was added to the filtrate and the solution heated to reflux for 45 minutes. The reaction mixture was then treated with decolourising charcoal (0.5 g), filtered, concentrated under reduced pressure and treated with aqueous hydrobromic acid (48% w/w HBr, 2.0 cm3). The solid which appeared upon refrigeration was recrystallised from aqueous ethanol to give 1-(2-nitro-1-imidazolyl)-3-(3-bromopropylamino)-2-propanol hydrobromide (6.87 g, 59.9%) as a hygroscopic yellow crystalline solid.
Workup
- filtrationthe mixture filtered
- temperaturethe solution heated
- temperatureto reflux for 45 minutes
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- additiontreated with aqueous hydrobromic acid (48% w/w HBr, 2.0 cm3)
- customwas recrystallised from aqueous ethanol
Sources & evidence
- ORD record
- ord-242b6d66a9ea426886a40d1965beacef
- Source dataset
- uspto-grants-1996_05
- Patent number
- US05521203
Reaction notes
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