Hydrochloric Acid → 1-[(3-Acetylphenyl)methyl]-3-(4-chlorophenyl)urea

Participants

Reaction Steps

A 2N HCl solution was added to a solution of 22 (165 mg, 0.479 mmol) in THF (2 mL). The mixture was refluxed for several hours until the starting materials were consumed. The reaction mixture was allowed to cool to room temperature, quenched with solid NaHCO3, and then the volatiles were removed under reduced pressure. The residue was diluted with ethyl acetate and then washed with water. The organic layer was dried over anhydrous MgSO4, filtered and concentrated. The residue was purified by chromatography to give 23 (144 mg, 100%) 1H NMR (DMSO-d, 400 MHz) δ 4.44 (d, J=5.6 Hz, 2H), 5.37 (t, J=3.7 Hz, 1H), 6.83 (s, 1H), 7.20-7.26 (5H, m), 7.40 (t, J=7.6 Hz, 1H), 7.50 (d, J=7.2 Hz, 1H), 7.82 (d, J=7.6 Hz, 1H), 7.85 (s, 1H); 13C NMR (DMSO-d6, 100 MHz) δ 27.45, 43.13, 119.85, 125.21, 127.11, 127.59, 129.13, 129.37, 132.61, 137.49, 140.07, 141.68, 155.73, 198.58; ESI-HRMS for C16H16N2O2Cl (M+H)+ calcd. 303.0900. found 303.0907.

Provenance & Evidence