Methane → 1-(2-Nitro-1-imidazolyl)-3-(3-bromopropylamino)-2-propanol hydrobromide

HRID 2372394

Reaktionsgleichung

[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]

Komponenten

Reaktionsbedingungen

Temperatur: 20 °C

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-afdc90622a674874b9d06aa2d0a323fd
Quelldatensatz: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05098921

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