Ethyl isothiocyanatoformate → Ethyl [(4,6-dichloropyridin-2-yl)carbamothioyl]carbamate

Participants

Reaction Steps

Ethoxycarbonyl isothiocyanate (2 g, 16 mmol) was added to a solution of 4,6-dichloropyridin-2-amine (2.2 g, 13 mmol) in 1,4-dioxane (100 mL) and stirred at rt for 18 h. LCMS showed desired product. The reaction mixture was concentrated in vacuo and the residue azeotroped with EtOAc (3×20 mL) to give a cream solid, which was triturated with EtOAc to give the desired product as a white solid (2.9 g, 76%). 1H NMR (DMSO) δ 12.31 (s, 1H), 11.77 (s, 1H), 8.86 (d, J=1.1 Hz, 1H), 7.66 (d, J=1.5 Hz, 1H), 4.25 (q, J=7.1 Hz, 2H), 1.28 (t, J=7.1 Hz, 3H). m/z [M+H]+=293.88

Provenance & Evidence