2-(2-Nitroimidazol-1-yl)acetic acid → N-(3-methyl-2-butenyl)-2-(2-nitro-1H-imidazol-1-yl)acetamide
Reaction equation
[N+:1]([C:4]1[N:5]([CH2:9][C:10]([OH:12])=O)[CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].C(C1NC=CN=1)(C1NC=CN=1)=O.Cl.[CH3:26][C:27]([CH3:31])=[CH:28][CH2:29][NH2:30].C([O-])(O)=O.[Na+]>CN(C=O)C.CO.ClCCl>[CH3:26][C:27]([CH3:31])=[CH:28][CH2:29][NH:30][C:10](=[O:12])[CH2:9][N:5]1[CH:6]=[CH:7][N:8]=[C:4]1[N+:1]([O-:3])=[O:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
2-(2-Nitro-1H-imidazol-1-yl)acetic acid (8.6 g, 50 mmol) was dissolved in DMF (50 mL). Carbonyl diimidazole [CDI] (8.7 g, 60 mmol) was added to the solution in small portions. The reaction mixture was stirred under N2 for 15 min. 3,3-Dimethylallylamine hydrochloride was suspended in DMF (50 mL) and stirred with NaHCO3 (4.2 g, 50 mmol). This suspension was added to the CDI and 2-(2-nitro-1H-imidazol-1-yl)acetic acid in DMF solution. The mixture was stirred under N2 atmosphere at room temperature overnight. TLC (silica gel, 10% methanol-dichloromethane) showed one spot with Rf =0.5, indicating completion of the reaction. DMF was evaporated on a rotary evaporator and the residue was triturated with ice-water (125 mL) and filtered. The solid was washed with cold water (3×50 mL) and dried in vacuum to give a white solid.
Workup
- stirringThe mixture was stirred under N2 atmosphere at room temperature overnight
- customcompletion of the reaction
- customDMF was evaporated on a rotary evaporator
- customthe residue was triturated with ice-water (125 mL)
- filtrationfiltered
- washThe solid was washed with cold water (3×50 mL)
- customdried in vacuum
- customto give a white solid
Sources & evidence
- ORD record
- ord-57e0c8e841d84c0da62bba5682501fe1
- Source dataset
- uspto-grants-1997_08
- Patent number
- US05656254
Reaction notes
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