Thiophosgene → 4-[2-(Dimethylamino)ethoxy]phenyl isothiocyanate

Participants

Reaction Steps

Diisopropylethylamine (344 mg, 2.66 mmol, 2.4 eq.) was added with stirring to a solution of 4-[2-(dimethylamino)ethoxy]aniline (200 mg, 1.11 mmol, 1 eq.) in tetrahydrofuran (2 mL) at 0° C., and then thiophosgene (153 mg, 1.33 mmol, 1.2 eq.) was added dropwise with stirring. The reaction mixture was allowed to warm to room temperature with stirring, and stirred at room temperature for 40 minutes, during which a precipitate formed. The tetrahydrofuran was removed under vacuum, and the residue was dissolved in ethyl acetate and washed with brine (3×10 mL), then the ethyl acetate layer dried over magnesium sulfate and the ethyl acetate evaporated to give 4-[2-(dimethylamino)ethoxy]phenyl isothiocyanate (0.20 g) as a dark brown oil, which was used without further purification.

Provenance & Evidence