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ChemicalBook CAS DataBase List Methyl 1-benzylbenzoiMidazole-5-carboxylate
185428-95-9

Methyl 1-benzylbenzoiMidazole-5-carboxylate synthesis

7synthesis methods
-

Yield:185428-95-9 47%

Reaction Conditions:

with toluene-4-sulfonic acid in toluene at 120; for 2 h;

Steps:

126-1 Preparation Example 126-1: synthesis of 1-benzyl-1H-benzimidazole-5-carboxylic acid methyl ester

3-Amino-4-benzylamine-benzoic acid methyl ester (500mg, 2.0mmol) obtained from Preparation Example 125-2 was dissolved in toluene (50ml), and triethylorthoformate (0.65ml, 4.0mmol) and p-toluenesulfonic acid (50mg) were added thereto. The mixture was stirred at 120 for 2 hours and then distilled under reduced pressure. Water was added thereto and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and filtered. Filtrate was distilled under reduced pressure and separated by column chromatography to obtain the title compound (250mg, 47%).[1466] NMR:1H-NMR(400HMz, CDCl3); 8.55 (s, 1H), 8.09 (s, 1H), 8.00 (d, 1H), 7.78 (d, 1H), 7.36 (m, 3H), 7.18 (m, 2H), 5.40 (s, 2H), 3.94 (s, 3H)

References:

WO2014/73904,2014,A1 Location in patent:Paragraph 1463-1466