2-Nitroimidazole → 3-[3-(2-Nitro-1H-imidazol-1-yl)propyl]-2-oxazolidinone
Reaction equation
[N+:1]([C:4]1[NH:5][CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].Cl[CH2:16][CH2:17][CH2:18][N:19]1[CH2:23][CH2:22][O:21][C:20]1=[O:24]>>[N+:1]([C:4]1[N:5]([CH2:16][CH2:17][CH2:18][N:19]2[CH2:23][CH2:22][O:21][C:20]2=[O:24])[CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2]Participants
4
Conditions
- Temperature
- 60 °C
Procedure
A mixture of 6 9 of 2-nitroimidazole (53 mmol) and 7.32 g of K2CO3 was heated at 60° C. for 0.5 hours. Then 8.6 g (53 mmol) of 3-(3-chloropropyl)-2-oxazolidinone (Ann. Pharm. Franc., 13, 565 (1955)) was added and stirring continued for 18 hours at 60° C. The mixture was then cooled and concentrated. The residue was partitioned between CHCl3 and water, the organic layer was dried and concentrated to give 10.4 g of a solid which was recrystallized from ethanol to provide 5.4 g (42%) of the desired product, 3-[3-(2-nitro-1H-imidazol-1-yl)propyl]-2-oxazolidinone; mp 89°-91° C.