3,4-Dimethylaniline → 2-(2,6-dichlorophenyl)-1-methyl-1H-benzoimidazole-5-carboxylic acid (3,4-dimethylphenyl)-amide

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Reaction Steps

To a mixture of 2-(2,6-dichlorophenyl)-1-methyl-1H-benzoimidazole-5-carboxylic acid (100 mg), EDCI (59 mg) and HOBt (42 mg) in DMF (2 mL) was added 3,4-dimethylaniline (38 mg) and the mixture was stirred at room temperature for 18 h. The mixture was poured into water and was extracted with EtOAc. The organic phase was washed with water (3×) and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue purified by flash chromatography using EtOAc/CH2Cl2 (1:5) as eluent to give 2-(2,6-dichlorophenyl)-1-methyl-1H-benzoimidazole-5-carboxylic acid (3,4-dimethylphenyl)-amide as a glasslike solid; MS (m/z) 424 (M+1); 1H NMR (CDCl3, 400 MHz) δ 8.36 (s, 1H), 8.24 (s, 1H), 8.00 d, J=8.59 Hz, 1H), 7.52-7.39 (m, 6H), 7.10 (d, J=8.08 Hz, 1H), 3.65 (s, 3H), 2.28 (s, 3H), 2.25 (s, 3H).

Provenance & Evidence