Thiophosgene → 2,3-Dimethyl-6-nitrophenyl isothiocyanate

Participants

Reaction Steps

To a solution of 2,3-dimethyl-6-nitroaniline (3.0 g, 1.0 equiv.) in toluene (150 mL) was added thiophosgene (2.5 mL, 1.8 equiv.) and the reaction mixture was heated at the reflux temp. overnight. The resulting mixture was concentrated under reduced pressure and the residue was purified by column chromatography (10% CH2Cl2/hex) to afford 2,3-dimethyl-6-nitrophenyl isothiocyanate as a light yellow solid (3.63 g, 95%): 1H NMR (CDCl3) δ2.39 (s, 3H), 2.40 (s, 3H), 7.17 (d, J=8.4 Hz, 1H), 7.83 (d, J=8.7 Hz, 1H).

Provenance & Evidence