1,1'-Thiocarbonyldi-2(1H)-pyridone → 4-(4-isothiocyanato-2-methoxyphenyl)-1-methyl-1H-pyrazole

Participants

Reaction Steps

Step K (3): Dichloromethane (25 mL) was added to a flask charged with 3-methoxy-4-(1-methyl-1H-pyrazol-4-yl)aniline (1.5 g, 7.38 mmol) and 1,1′-thiocarbonyldipyridin-2(1H)-one (2.57 g, 11.1 mmol). The resulting mixture was stirred for 16 h at rt. The reaction mixture was concentrated in vacuo. The crude products were purified using silica gel chromatography (30% EtOAc/dichloromethane). The fractions containing product were combined and concentrated. The resulting solid was recrystallized from hexane to afford 4-(4-isothiocyanato-2-methoxyphenyl)-1-methyl-1H-pyrazole (1.46 g, 5.95 mmol, 81% yield) as a light yellow solid. LC-MS (M+H)+ 272.0. 1H NMR (500 MHz, chloroform-d) δ ppm 7.57 (d, J=1.83 Hz, 1 H) 7.07 (d, J=1.53 Hz, 1 H) 6.94-7.04 (m, 2 H).

Provenance & Evidence