HCID 54544079, compound → 1-(prop-2-en-1-yl)-1H-imidazol-2-amine
Reaction equation
CN(C=[N:5][C:6]1[N:7]([CH2:11][CH:12]=[CH2:13])[CH:8]=[CH:9][N:10]=1)C>Cl>[NH2:5][C:6]1[N:7]([CH2:11][CH:12]=[CH2:13])[CH:8]=[CH:9][N:10]=1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
2-(Dimethylaminomethylene)amino-1-(2-propenyl)imidazole (0.2 g) was dissolved in 6N hydrochloric acid (5 ml), and the solution was heated under reflux for 1 hour. The solvent was evaporated under reduced pressure, and the resulting residue was dissolved in aqueous saturated sodium carbonate solution (1 ml). The solution was concentrated under reduced pressure, the organic compounds were extracted with chloroform, and the solvent was evaporated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (eluent: chloroform-methanol-ammonia water=20: 1:0.1) to give 2-amino-1-(2-propenyl)imidazole. This compound was dissolved in dichloromethane, and 4N hydrochloric acid-ethyl acetate (2 ml) was added to form its hydrochloric acid salt. The salt was recrystallized from acetonitrile to give 2-amino-1-(2-propenyl)imidazole hydrochloride (0.19 g, Yield: 71%) as pale yellow needles.
Workup
- temperaturethe solution was heated
- temperatureunder reflux for 1 hour
- customThe solvent was evaporated under reduced pressure
- dissolutionthe resulting residue was dissolved in aqueous saturated sodium carbonate solution (1 ml)
- concentrationThe solution was concentrated under reduced pressure
- extractionthe organic compounds were extracted with chloroform
- customthe solvent was evaporated under reduced pressure
- customThe resulting residue was purified by column chromatography on silica gel (eluent: chloroform-methanol-ammonia water=20: 1:0.1)
Sources & evidence
- ORD record
- ord-1e6a88c6fc1e4f0ea5668eff0b407ac1
- Source dataset
- uspto-grants-1996_09
- Patent number
- US05552427
Reaction notes
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