Benzyl Bromide → HCID 70675030, compound

Participants

Reaction Steps

To N-(adamantan-2-yl)-2-(1,1-dioxido-1,2,6-thiadiazinan-2-yl)acetamide hydrochloride (50 mg, 0.135 mmol) in DMF (1 mL), were added K2CO3 (93.3 mg, 0.675 mmol) and (bromomethyl)benzene (46.2 mg, 0.27 mmol). The reaction mixture was agitated for 4 hr at room temperature and extracted with ethyl acetate and brine. The organic layer was dried over MgSO4 and the residue was purified by silica gel column chromatography to yield N-(adamantan-2-yl)-2-(6-benzyl-1,1-dioxido-1,2,6-thiadiazinan-2-yl)acetamide (53 mg, 94%, white solid). 1H NMR (300 MHz, DMSO-d6): δ 7.72-7.69 (brd, 1H), 7.39-7.28 (m, 5H), 4.17 (s, 2H), 3.86-3.83 (m, 1H), 3.79 (s, 2H), 3.46-3.42 (m, 2H), 3.17-3.14 (m, 2H), 1.93-1.89 (m, 2H), 1.80-1.67 (m, 12H), 1.52-1.48 (m, 2H).

Provenance & Evidence