5-CARBOXYBENZIMIDAZOLONE METHYL ESTER Chemical Properties

Melting point:

312-313°

Boiling point:

221.2±19.0 °C(Predicted)

Density 

1.325±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

11.54±0.30(Predicted)

Appearance

Light brown to gray Solid

Safety Information

HazardClass 

IRRITANT

5-CARBOXYBENZIMIDAZOLONE METHYL ESTER Usage And Synthesis

Synthesis

Methyl 3,4-diaminobenzoate (5.00 g, 30.1 mmol) was dissolved in THF (40 mL) at 0 °C, followed by the addition of N,N'-carbonyldiimidazole (7.32 g, 45.1 mmol). The reaction mixture was stirred at 0 °C for 16 h and gradually warmed up to 23 °C. Upon completion of the reaction, 1M HCl aqueous solution (50 mL) was slowly added followed by water (70 mL) at 0 °C and stirring was continued for 1 hour. The resulting precipitate was collected by filtration and dried under reduced pressure for 18 h to afford methyl 2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylate (5.45 g, 94% yield), and the product could be used for subsequent reactions without further purification. Mass spectrum (ESI/CI): calculated value C9H8N2O3, 192.1; measured value m/z 193.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ: 11.01 (s, 1H), 10.84 (s, 1H), 7.63 (dd, J=8.2,1.6Hz, 1H), 7.47 (s, 1H). 7.02 (d, J=8.2Hz, 1H), 3.82 (s, 3H).

References

[1] Patent: WO2009/134750, 2009, A1. Location in patent: Page/Page column 139
[2] Journal of Medicinal Chemistry, 2006, vol. 49, # 12, p. 3719 - 3742
[3] Patent: US2010/249124, 2010, A1. Location in patent: Page/Page column 62
[4] Cell Chemical Biology, 2018, vol. 25, # 6, p. 677 - 12,690

5-CARBOXYBENZIMIDAZOLONE METHYL ESTER(106429-57-6)Related Product Information

• METHYL 2-OXO-1-PIPERIDIN-4-YL-2,3-DIHYDRO-1H-BENZOIMIDAZOLE-5-CARBOXYLATE
• 2-OXO-2,3-DIHYDRO-1H-BENZOIMIDAZOLE-5-CARBOXYLIC ACID
• 5-CARBOXYBENZIMIDAZOLONE METHYL ESTER
• ethyl 1-ethyl-2-oxo-2,3-dihydro-1H-benzimidazole-5-carboxylate
• METHYL 2-OXO-3-PIPERIDIN-4-YL-2,3-DIHYDRO-1H-BENZOIMIDAZOLE-5-CARBOXYLATE