Methyl 2-ethoxybenzimidazole-7-carboxylate Chemical Properties

Boiling point:

373.1±34.0 °C(Predicted)

Density 

1.269

storage temp. 

2-8°C

solubility 

soluble in Chloroform, Methanol

form 

Solid

pka

8.99±0.30(Predicted)

color 

Dark Reddish Orange to Dark Brown

InChI

InChI=1S/C11H12N2O3/c1-3-16-11-12-8-6-4-5-7(9(8)13-11)10(14)15-2/h4-6H,3H2,1-2H3,(H,12,13)

InChIKey

MOPLKVMMSFGZIR-UHFFFAOYSA-N

SMILES

C1(OCC)NC2=C(C(OC)=O)C=CC=C2N=1

Methyl 2-ethoxybenzimidazole-7-carboxylate Usage And Synthesis

Chemical Properties

Dark Reddish Orange Solid

Uses

An intermediate in the preparation of labelled Candesartan.

Synthesis

1. Methyl 2-amino-3-nitrobenzoate (150.0 g, 0.765 mol) was placed in an autoclave and ethyl acetate (1000 mL) and nickel ruanne (75 g) were added. The reaction mixture was stirred at 12-15 °C for 20-25 h under hydrogen pressure (2-3 kg/cm2). Upon completion of the reaction, the catalyst was removed by diatomaceous earth filtration and the diatomaceous earth was washed with ethyl acetate (150 mL). The filtrate was distilled under reduced pressure and the solvent was completely removed at 45-50 °C. 2. Acetic acid (171 mL) was added to the residue, and raw tetraethyl carbonate (180 g) was added slowly over 30-45 minutes. The reaction mixture was stirred at 25-35 °C for 2-3 hours. 3. Cool the reaction mixture to 0-5 °C and slowly add water (750 mL) over 15-30 min. The precipitated solid was filtered and washed sequentially with water (150 mL) and ethyl acetate (150 mL). 4. The resulting solid was dried at 55-65 °C for 10-12 h to afford methyl 2-ethoxy-1H-benzo[d]imidazole-7-carboxylate (140 g, 83.1% yield).

References

[1] Patent: WO2006/15134, 2006, A1. Location in patent: Page/Page column 15; 16
[2] Patent: CN104876877, 2018, B. Location in patent: Paragraph 0033; 0069-0072

Methyl 2-ethoxybenzimidazole-7-carboxylate(150058-27-8)Related Product Information

• Azilsartan Impurity
• Methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate
• Methyl 3-aMino-2-((2'-carbaMoylbiphenyl-4-yl)MethylaMino)benzoate
• 1-[[2'-(AMinoiMinoMethyl)[1,1'-biphenyl]-4-yl]Methyl]-2-ethoxy-1H-benziMidazole-7-carboxylic Acid
• Azilsartan iMpurity
• Ethyl -2-ethoxy-1-[[(2-(1Htetrazol-5-yl)biphenyl-4-yl-) methyl]
• BENZOIC ACID, 2-[[(2'-CYANO[1,1'-BIPHENYL]-4-YL)METHYL]AMINO]-3-NITRO-METHYL ESTER
• 2-[1.1-dimethyl ethyl ethoxy carbonyl]amino-3-nitro benzoic acid ethyl ester
• Ethyl-3-Amino-2-[(2'-Cyanoiphenyl-4-yl) Methyl]-Amino Benzoate
• Ethyl-2-Ethoxy-1-[[(2'-(1h-Tetrazol-5-Yl)Biphenyl-4-Yl)Methyl]Benzimidazole]-7-Carboxylate