4-Methylphenyl isocyanate → HCID 9843254, compound

Participants

Reaction Steps

p-Tolyl isocyanate (0.19 mL, 1.55 mmol) was added to a solution of 2-methoxy-5-(trifluoromethanesulfonyl)aniline (0.330 g, 1.29 mmol) in EtOAc (5 mL), and the reaction mixture was stirred at room temp. for 18 h. The resulting precipitate was collected by filtration and washed with Et2O to give a white solid (0.28 g). This material was then purified by HPLC (C-18 column, 50% CH3CN/50% H2O) and the resulting solids were triturated with Et2O to provide the title compound (0.198 g): 1H-NMR (CDCl3) δ 7.08 (d, J=8.5 Hz, 2H), 7.33 (d, J=8.5 Hz, 2H), 7.40 (d, J=8.8 Hz, 1H), 7.71 (dd, J=2.6, 8.8 Hz, 1H), 8.66 (s, 1H), 8.90 (d, J=2.6 Hz, 1H), 9.36 (s, 1H); FAB-MS m/z 389 ((M+1)+). B1c. General Method for the Reaction of an Aryl Amine with an Aryl Isocyanate

Provenance & Evidence