3-Chloro-4-methylphenyl isocyanate → HCID 66784893, compound

Participants

Reaction Steps

2-(piperidin-3-yl)-1H-benzo[d]imidazole (100.0 mg, 0.497 mmol) was dissolved in dichloromethane (3.0 mL). To the stirred suspension was added 2-chloro-4-isocyanato-1-methylbenzene (84.1 mg, 0.502 mmol). The reaction was stirred at ambient temperature for one hour. The crude mixture was then concentrated in vacuo and the residue was dissolved in minimal amounts of dimethylformamide and purified via preparative HPLC (10%-50% acetonitrile in water). The pure fractions were combines and lyophilized to yield the title compound 1 as a fluffy white solid (147.5 mg, 63.7%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.55-1.65 (m, 1H), 1.83 (d, J=13.73 Hz, 1H), 1.97 (q, 0.1=18.28 Hz, 1H), 2.25 (s, 3H), 2.30 (s, 1H), 2.99 (t, J=11.44 Hz, 1H), 3.23 (t, J=13.34 Hz, 1H), 3.34-3.38 (m, 1H), 4.11 (d, J=13.35 Hz, 1H), 4.48 (d, J=13.35 Hz, 1H), 7.20 (d, J=8.4 Hz, 1H), 7.32 (d, J=8.5 Hz, 1H), 7.51-7.34 (m, 1H), 7.63 (s, 1H), 7.78-7.80 (m, 1H), 8.76 (s, 1H), ESI-MS: m/z 369.2 (M+H)+.

Provenance & Evidence