Thiophosgene → 2-Isothiocyanatopyridine

Participants

Reaction Conditions

Reaction Steps

A solution of 2-aminopyridine (0.94 g, 9.99 mmol, Sigma Aldrich) and TEA (3.06 mL, 21.97 mmol) in THF (40.0 mL) was set stirring at 0° C. under nitrogen. A solution of thiophosgene (0.804 mL, 10.49 mmol, Fluka) in 2 mL THF was added dropwise over 5 minutes, and the reaction was stirred for 3 h at 0° C. Silica was added, and the reaction mixture was adsorbed under reduced pressure. It was purified on 16 g SiO2 (eluent: 0-100% EtOAc/hexanes over 30 min, RediSep Gold). The product fractions containing the product by TLC (50% EtOAc/hexanes) were combined and concentrated under reduced pressure to give 2-isothiocyanatopyridine (852 mg, 63%). m/z (ESI, +ve) 137.0 (M+H)+.

Provenance & Evidence