2-Amino-4-methylphenol → N-(4-Bromophenyl)-5-methyl-1,3-benzoxazol-2-amine

Participants

Reaction Steps

2-Amino-4-methylphenol (1.15 g, 9.34 mmol) was added to a solution of 4-bromophenyl isothiocyanate (2.00 g, 9.34 mmol) in tetrahydrofuran (35 mL) and the reaction was stirred at room temperature for 16 h. Anhydrous copper (II) sulfate (14.06 g, 88.10 mmol), silica gel (14.06 g), and triethylamine (1.3 mL, 9.34 mmol) were added, and the mixture was stirred at room temperature for 24 h. The reaction was concentrated under reduced pressure and then added to a silica pad and purified using 1:5 ethyl acetate:heptane (2 L) followed by diethyl ether as the eluent to afford N2-(4-bromophenyl)-5-methyl-1,3-benzoxazol-2-amine as a light brown solid (2.30 g, 81%); RP-HPLC Rt 16.437 min, 94% purity (5% to 85% acetonitrile/0.1M aqueous ammonium acetate, buffered to pH 4.5, over 20 min at 1 mL/min; λ=254 nm; Deltapak C18, 300 Å, 5 μm, 150×3.9 mm column); 1H NMR (400 MHz, d6-DMSO) 2.37 (3H, s), 6.94 (1H, d, J=8.1 Hz), 7.27 (1H, s), 7.36 (1H, d, J=8.1 Hz), 7.54 (2H, d, J=8.4 Hz), 7.72 (2H, d, J=8.4 Hz), and 10.72 (1H, s).

Provenance & Evidence