ETHYL 1-METHYL-5-NITROIMIDAZOLE-2-CARBOXYLATE Chemical Properties

Melting point:

81-83°C

Boiling point:

350.7±34.0 °C(Predicted)

Density 

1.42±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

pka

-0.95±0.25(Predicted)

Appearance

White to off-white Solid

ETHYL 1-METHYL-5-NITROIMIDAZOLE-2-CARBOXYLATE Usage And Synthesis

Synthesis

Step 6a. ethyl 1-methyl-1H-imidazole-2-carboxylate (2.0 g, 13 mmol) was dissolved in 8 mL of concentrated H2SO4, followed by the slow addition of 8 mL of concentrated HNO3. The reaction mixture was stirred at 70 °C for 3 h. The reaction mixture was then extracted with dichloromethane (DCM). After completion of the reaction, the solution was diluted with H2O and the pH was adjusted to 7-8 with aqueous Na2CO3. The reaction mixture was extracted with dichloromethane (DCM) and the organic layers were combined and concentrated. Purification by silica gel column chromatography (eluent: ethyl acetate/petroleum ether) afforded the target compound 1-methyl-5-nitro-1H-imidazole-2-carboxylic acid ethyl ester as a yellow solid (0.9 g, 34.7% yield).ESI-MS m/z = 200.20 [M + H]+.

References

[1] Patent: WO2016/183266, 2016, A1. Location in patent: Page/Page column 50