Hydrogen Bromide → 2-Bromo-5-nitrothiazole
Reaktionsgleichung
N[C:2]1[S:3][C:4]([N+:7]([O-:9])=[O:8])=[CH:5][N:6]=1.N([O-])=O.[Na+].[BrH:14]>O.CCCCCO>[Br:14][C:2]1[S:3][C:4]([N+:7]([O-:9])=[O:8])=[CH:5][N:6]=1Komponenten
6
N[C:2]1[S:3][C:4]([N+:7]([O-:9])=[O:8])=[CH:5][N:6]=1.N([O-])=O.[Na+].[BrH:14]>O.CCCCCO>[Br:14][C:2]1[S:3][C:4]([N+:7]([O-:9])=[O:8])=[CH:5][N:6]=1To 72.5 g of 2-amino-5-nitrothiazole in 300 mL of 48% hydrobromic acid and 200 mL of water stirred and cooled to about -10° C. was slowly added, in portions, 51.8 g of sodium nitrite dissolved in 80 mL of water from one addition funnel and 250 mL of n-amyl alcohol from a second addition funnel. The addition of both solutions required about 3 hours. The cooling bath was removed and the mixture allowed to warm to about 15° C. overnight and then stirred at room temperature for 2 hours. The solid was collected by vacuum filtration and steam distilled to give 67 g of crude product. The crude product was recrystallized from hot ethanol to give 61 g (60% yield) of the 2-bromo-5-nitrothiazole as a yellow solid.
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