Hydrochloric Acid → Benzenamine, 2,4,6-trimethyl-, hydrochloride (1:1)

Participants

Reaction Steps

A solution of 2,4,6-trimethyl-phenylamine (13.5 g, 100 mmol) in diethyl ether (50 mL) was added to a vigorously stirred solution of hydrogen chloride in diethyl ether (1.0 M, 100 mL, 100 mmol) at 0° C., followed by stirring at room temperature for 30 minutes. Removal of the solvent under reduced pressure afforded 2,4,6-trimethyl-phenylamine hydrochloride as an off-white solid (17.2 g, 100%), which was suspended in ethanol (100 mL) and treated with cyanamid (5.0 g, 120 mmol). The resulting solution was heated to reflux for 43 hours and then concentrated under reduced pressure. The viscous residue so obtained was triturated with diethyl ether (2×100 mL) to afford the guanidine hydrochloride IV as an hygroscopic, light brown foam (22 g, 100%; ESIMS m/z (M+H)=178).

Provenance & Evidence