Hydrochloric Acid → Ethyl 2-amino-1-methyl-1H-imidazole-5-carboxylate

Temperature

0 °C

Potassium-t-butoxide (52.3 g) was suspended in diethylether (500 ml) and cooled to 0° C. A solution of N-formyl sarcosine ether ester (67.66 g) and methyl formate (27.9 g) in diethylether (200 ml) was added dropwise over 30 minutes and the mixture was stirred at 0° C. for 1 hour. The solid product was filtered (76.6 g) and used immediately for the next stage. The ethyl-2-(N-formyl-N-methyl)-3-oxopropionate prepared as described above was dissolved in water and concentrated HCl (138 ml) was added. The mixture was heated on a steam bath for 30 minutes, cooled and the pH was adjusted to 5 by addition of concentrated NaOH. Cyanamide (19.3 g) was added and the mixture was heated at 100° C. for 1 hour. The mixture was allowed to cool and was basified with concentrated aqueous ammonium hydroxide, the solid was filtered, washed with water and dried under reduced pressure and was crystallised from EtOAc (300 ml) to give ethyl 2-amino-1-methyl-1H-imidazole-5-carboxylate yield 14.6 g.

1. filtrationThe solid product was filtered (76.6 g)
2. customThe ethyl-2-(N-formyl-N-methyl)-3-oxopropionate prepared
3. temperatureThe mixture was heated on a steam bath for 30 minutes
4. temperaturecooled
5. temperaturethe mixture was heated at 100° C. for 1 hour
6. temperatureto cool
7. filtrationthe solid was filtered
8. washwashed with water
9. customdried under reduced pressure
10. customwas crystallised from EtOAc (300 ml)

ORD record

ord-fe601c17fa9f4c548a4ad038deaa1f87

Source dataset

uspto-grants-1998_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05843942