Potassium Carbonate → ethyl 1-amino-1H-imidazole-2-carboxylate

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 (11.0 g, 78.6 mmol, 1.0 eq) was added and the resulting mixture was stirred at 90° C. for 30 min. The mixture was cooled to RT and K2CO3 (3.6 g, 26.2 mmol, 1.0 eq) was added in portions. The resulting mixture was stirred at RT overnight, filtered and rinsed with H2O (10 mL×3). The filtrate was extracted with ethyl acetate (50 mL×5). The combined organic layer was washed with brine, dried over Na2SO4 and filtered. The filtrate was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel (1% MeOH in DCM) to afford ethyl 1-amino-1H-imidazole-2-carboxylate (800 mg, 6.5% yield). ESI-MS m/z: 156.1 [M+H]+.

1. temperatureThe mixture was cooled to RT
2. stirringThe resulting mixture was stirred at RT overnight
3. filtrationfiltered
4. washrinsed with H2O (10 mL×3)
5. extractionThe filtrate was extracted with ethyl acetate (50 mL×5)
6. washThe combined organic layer was washed with brine
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. customThe filtrate was evaporated in vacuo
10. customthe residue was purified by flash column chromatography on silica gel (1% MeOH in DCM)

ORD-Eintrag

ord-e036681f841d4af4a8196ba80e20d003

Quelldatensatz

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08969363B2