Ethyl Acetate → HCID 58156326, compound

Participants

Reaction Steps

To a solution of 2-(2,6-dichlorophenyl)-3H-benzimidazol-5-ylamine (100 mg, 360 μmol) in THF (5 mL) was added 3,4-dimethylphenylisocyanate (51 μL, 54 mg., 360 μmols) and the mixture was stirred at ambient temperature for 18 h then was poured into ethyl acetate and extracted with water. The organic layer was dried, filtered, and solvent removed under reduced pressure to leave crude product that was purified by chromatography using a 50-90% gradient of heptane/ethyl acetate to give 1-[2-(2,6-dichlorophenyl)-3H-benzimidazol-5-yl]-3-(3,4-dimethylphenyl)-urea. 1H NMR (DMSO-d6, 400 MHz): δ 12.69 (s, broad, 1H), 8.69 (s, broad, 1H), 8.48 (s, 1H), 7.95 (s, broad, 1H), 7.67 (d, J=7.7 Hz, 2H), 7.60 (m, 2H), 7.26 (s, 1H), 7.20 (d, J=7.7 Hz, 1H) 7.03 (d, J=8.0 Hz, 2H), 2.20 (s, 3H), 2.16 (s, 3H); MS (m/z) 425.1 (M+1); Retention time=1.35 min (Method 10); High Resolution MS (M+1): theory 425.0936, measured 425.0951.

Provenance & Evidence