2-Methylbenzylamine → HCID 11652890, compound

Participants

Reaction Steps

2-Methylbenzylamine (89.1 mg, 0.735 mmol) in 8 ml of dry THF was treated with 2,3-dichlorophenylisothiocyanate (150 mg, 0.735 mmol). After stirring at room temperature for 1 hour, the mixture was treated with mercuric acetate (234.2 mg, 0.735 mmol) and sodium azide (143.3 mg, 2.21 mmol) and stirred at room temperature for 16 hours. The mixture was filtered through a pad of Celite and washed with ethyl acetate. The filtrate was concentrated under reduced pressure and purified by preparative HPLC on a Waters Symmetry C8 column (40 mm×100 mm, 7 μm particle size) using a gradient of 10% to 100% acetonitrile to ammonium acetate (10 mM) over 15 minutes at a flow rate of 70 mL/min to provide the title compound. MS (ESI+) m/z 334 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 2.29 (s, 3 H), 4.46 (d, J=5.42 Hz, 2 H), 7.16 (m, 3 H), 7.26 (m, 1 H), 7.57 (t, J=5.42 Hz, 1 H), 7.60 (t, J=8.14 Hz, 1 H), 7.71 (dd, J=7.97, 1.53 Hz, 1 H), 7.93 (dd, J=8.14, 1.70 Hz, 1 H).

Provenance & Evidence