Identification | Back Directory | [Name]
5-CARBOXYBENZIMIDAZOLONE METHYL ESTER | [CAS]
106429-57-6 | [Synonyms]
5-CARBOXYBENZIMIDAZOLONE METHYL ESTER Methyl 2-Oxo-2,3-dihydrobenzimidazole-5-carboxylate Methyl 2-oxo-1,3-dihydro-1,3-benzodiazole-5-carboxylate methyl 2-oxo-2,3-dihydro-1H-1,3-benzodiazole-5-carboxylate Methyl 2-oxo-2,3-dihydro-1H-benzo[d]iMidazole-5-carboxylate methyl 2-oxo-2,3-dihydro-1H-1,3-benzimidazole-5-carboxylate 2-Oxo-2,3-dihydro-1H-benzoimidazole-5-carboxylic acid methyl ester 1H-Benzimidazole-5-carboxylic acid, 2,3-dihydro-2-oxo-, methyl ester 1H-Benzimidazole-5-carboxylicacid,2,3-dihydro-2-oxo-,methylester(9CI) | [EINECS(EC#)]
200-110-4 | [Molecular Formula]
C9H8N2O3 | [MDL Number]
MFCD08457979 | [MOL File]
106429-57-6.mol | [Molecular Weight]
192.17 |
Chemical Properties | Back Directory | [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 |
Hazard Information | Back Directory | [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 |
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