Dimethylamine, hydrochloride → HCID 53728357, compound

Participants

Reaction Steps

N-Chlorosuccinimide (1 g) was added portionwise to 7-methoxybenzofuran-2-sulfinic acid, lithium salt (1.47 g) in dichloromethane (15 ml) at 0-5° C. under an inert atmosphere. The reaction was stirred at this temperature for 15 minutes and then warmed to ambient temperature and stirred for a further 15 minutes. The mixture was then flushed through a pad of celite, washing well with dichloromethane. The solvent was removed in vacuo to give a tan solid as the crude intermediate. This intermediate was added to a stirred solution of dimethylamine hydrochloride (0.67 g) and triethylamine (2.2 ml) in tetrahydrofuran (20 ml) at 0-5° C. under an inert atmosphere. The reaction was stirred at this temperature for 1 h and then warmed to room temperature and stirred for a further 48 h. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (2×40 ml) and water (50 ml). The combined organic phases were washed with 1M hydrochloric acid (2×20 ml), dried over magnesium sulfate and concentrated in vacuo. The residue was washed with hexane (40 ml) to give the title compound as a tan solid (0.88 g).

Provenance & Evidence