Methyl 1,2-diMethyl-1H-benzo[d]iMidazole-5-carboxylate

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Methyl 1,2-diMethyl-1H-benzo[d]iMidazole-5-carboxylate Basic information
Product Name:Methyl 1,2-diMethyl-1H-benzo[d]iMidazole-5-carboxylate
Synonyms:Methyl 1,2-diMethyl-1H-benzo[d]iMidazole-5-carboxylate;1H-BenziMidazole-5-carboxylic acid, 1,2-diMethyl-, Methyl ester;Methyl 1,2-diMethyl-1H-1,3-benzodiazole-5- carboxylate;Methyl 1,2-diMethyl-1,3-benzodiazole-5-carboxylate;1, 2-dimethyl-1h-benzo [d] imidazole-5-carboxylate methyl ester;methyl 1,2-dimethylbenzimidazole-5-carboxylate
CAS:256936-11-5
MF:C11H12N2O2
MW:204.23
EINECS:
Product Categories:
Mol File:256936-11-5.mol
Methyl 1,2-diMethyl-1H-benzo[d]iMidazole-5-carboxylate Structure
Methyl 1,2-diMethyl-1H-benzo[d]iMidazole-5-carboxylate Chemical Properties
Melting point 161~163℃
Boiling point 364.2±15.0 °C(Predicted)
density 1.20±0.1 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
pka5.51±0.25(Predicted)
AppearanceWhite to off-white Solid
Safety Information
MSDS Information
Methyl 1,2-diMethyl-1H-benzo[d]iMidazole-5-carboxylate Usage And Synthesis
Synthesis
Methanol

67-56-1

1H-Benzimidazole-5-carboxylicacid,1,2-dimethyl-(9CI)

90915-18-7

Methyl 1,2-diMethyl-1H-benzo[d]iMidazole-5-carboxylate

256936-11-5

1,2-Dimethyl-1H-benzo[d]imidazole-5-carboxylic acid (1.00 g, 5.26 mmol) was dissolved in methanol (20 mL) and stirred at room temperature. Concentrated sulfuric acid (0.6 mL) was slowly added to the solution. The reaction mixture was heated to reflux with continuous stirring overnight. Upon completion of the reaction, the mixture was cooled to room temperature and the reaction solution was neutralized with saturated aqueous sodium bicarbonate solution (100 mL) and subsequently extracted with ethyl acetate (3 x 100 mL). The organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford methyl 1,2-dimethyl-1H-benzo[d]imidazole-5-carboxylate (810 mg, 75% yield) as a yellow oil. Thin layer chromatography (TLC) showed an Rf value of 0.69 (unfolding agent ratio 85:15 dichloromethane/methanol). Nuclear magnetic resonance hydrogen spectrum (1H NMR, 300 MHz, CDCl3) δ: 2.61 (s, 3H), 3.72 (s, 3H), 3.92 (s, 3H), 7.27 (d, J=8.5 Hz, 1H), 7.98 (d, J=8.2 Hz, 1H), 8.35 (s, 1H). Mass spectrum (APCI MS) m/z: 205 [C11H12N2O2+H]+.

References[1] Organic Letters, 2008, vol. 10, # 6, p. 1183 - 1186
[2] Patent: WO2004/67529, 2004, A1. Location in patent: Page 213 - 214
Methyl 1,2-diMethyl-1H-benzo[d]iMidazole-5-carboxylate Preparation Products And Raw materials
Raw materialsMethanol-->1H-Benzimidazole-5-carboxylicacid,1,2-dimethyl-(9CI)
Tag:Methyl 1,2-diMethyl-1H-benzo[d]iMidazole-5-carboxylate(256936-11-5) Related Product Information
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