Thiophosgene → 5-isothiocyanato-N,N,4-trimethylpyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

Thiophosgene (9.3 mL, 125 mmol) was added dropwise to a stirred mixture of N2,N2,4-trimethylpyridine-2,5-diamine (15.7 g) in tetrahydrofuran (100 mL) and saturated aqueous sodium hydrogen carbonate (150 mL) at 0° C., and the mixture was stirred at 0° C. for 2 hr. The mixture was diluted with saturated aqueous sodium hydrogen carbonate, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was washed with n-hexane to give the title compound as a colorless powder (14.1 g, 73.0 mmol, 70% in 2 steps).

Provenance & Evidence