Ethyl chloroformate → Ethyl (1-methyl-1H-imidazol-2-yl)carbamate
Reaction equation
[C:1](Cl)(=[O:5])[O:2][CH2:3][CH3:4].Cl.[NH2:8][C:9]1[N:10]([CH3:14])[CH:11]=[CH:12][N:13]=1>N1C=CC=CC=1>[CH2:3]([O:2][C:1]([NH:8][C:9]1[N:10]([CH3:14])[CH:11]=[CH:12][N:13]=1)=[O:5])[CH3:4]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
Ethyl chlorocarbonate (0.6 g) was added to a solution of 2-amino-1-methylimidazole hydrochloride (0.3 g) in pyridine (5 ml), and the mixture was stirred under heating at 100° C. for 2 hours. The solvent was evaporated under reduced pressure, the residue was dissolved in water, and sodium carbonate was added until the solution became alkaline. The solvent was evaporated under reduced pressure, and then the residue was purified by column chromatography on silica gel (eluent: chloroform) to give 2-ethoxycarbonylamino-1-methylimidazole. This compound was dissolved in dichloromethane, and 4N hydrochloric acid-ethyl acetate (2 ml) was added to form its hydrochloric acid salt. The resulting crude crystals were washed with ether to give 2-ethoxycarbonylamino-1-methylimidazole hydrochloride (0.29 g, Yield: 56%) as colorless prisms.
Workup
- customThe solvent was evaporated under reduced pressure
- dissolutionthe residue was dissolved in water
- additionsodium carbonate was added until the solution
- customThe solvent was evaporated under reduced pressure
- customthe residue was purified by column chromatography on silica gel (eluent: chloroform)
Sources & evidence
- ORD record
- ord-9d6234d79398474d947f533661f03d54
- Source dataset
- uspto-grants-1996_09
- Patent number
- US05552427
Reaction notes
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