2,6-Dichloro-isonicotinoyl chloride → 1-(2,6-Dichloro-pyridine-4-carbonyl)-3-(2,3,4-trifluoro-phenyl)-thiourea

Participants

Reaction Steps

Ammonium isothiocyanate (7.726 g, 0.1015 mol) was added to a solution of 2,6-dichloro-4-pyridinecarbonyl chloride (17.8 g, 0.0846 mol) in acetone (300 ml). The mixture was stirred for 30 minutes and subsequently 2,3,4-trifluorobenzenamine hydrochloric acid (.HCl) was added slowly. The reaction mixture was stirred at room temperature for 2 hours and was then quenched with H2O (100 ml). The mixture was extracted with CH2Cl2 (3×80 ml) and the combined organic layers were dried (MgSO4), filtered and the solvent was evaporated in vacuo. The residue was purified by flash chromatography (eluent: heptane/EtOAc from 80/20 to 50/50). The desired fractions were collected and the solvent was evaporated in vacuo. Yield: 22.2 g of intermediate D9 (69%).

Provenance & Evidence