Potassium Carbonate → ethyl 1-amino-1H-imidazole-2-carboxylate
Reaction equation
[NH2:1]OS(O)(=O)=O.[NH:7]1[CH:11]=[CH:10][N:9]=[C:8]1[C:12]([O:14][CH2:15][CH3:16])=[O:13].C([O-])([O-])=O.[K+].[K+]>O>[NH2:1][N:7]1[CH:11]=[CH:10][N:9]=[C:8]1[C:12]([O:14][CH2:15][CH3:16])=[O:13]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
To a stirred solution of hydroxylamine-o-sulfonic acid (26.64 g, 235.8 mmol, 3.0 eq) in H2O (17 mL) at 0° C., ethyl 1H-imidazole-2-carboxylate (C-3) (11.0 g, 78.6 mmol, 1.0 eq) is added and the resulting mixture is stirred at 90° C. for 30 min. The mixture is cooled to RT and K2CO3 (3.6 g, 26.2 mmol, 1.0 eq) is added in portions. The resulting mixture is stirred at RT overnight, filtered and rinsed with H2O (10 mL×3). The filtrate is extracted with ethyl acetate (50 mL×5). The combined organic layer is washed with brine, dried over Na2SO4 and filtered. The filtrate is evaporated in vacuo and the residue is purified by flash column chromatography on silica gel (1% MeOH-DCM) to afford the product, ethyl 1-amino-1H-imidazole-2-carboxylate (C-4) as a colorless oil.
Workup
- temperatureThe mixture is cooled to RT
- stirringThe resulting mixture is stirred at RT overnight
- filtrationfiltered
- washrinsed with H2O (10 mL×3)
- extractionThe filtrate is extracted with ethyl acetate (50 mL×5)
- washThe combined organic layer is washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- customThe filtrate is evaporated in vacuo
- customthe residue is purified by flash column chromatography on silica gel (1% MeOH-DCM)
Sources & evidence
- ORD record
- ord-dc6ce4d30c57473fb96f988eb5da93e9
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08604032B2
Reaction notes
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