1,1'-Thiocarbonyldi-2(1H)-pyridone → 5-(4-Isothiocyanato-2-methoxyphenyl)-3-methylpyridazine
Reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][C:10]=1[C:11]1[CH:16]=[C:15]([CH3:17])[N:14]=[N:13][CH:12]=1)[NH2:7].[C:18](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:19]>ClCCl>[N:7]([C:6]1[CH:8]=[CH:9][C:10]([C:11]2[CH:16]=[C:15]([CH3:17])[N:14]=[N:13][CH:12]=2)=[C:4]([O:3][CH3:2])[CH:5]=1)=[C:18]=[S:19]Participants
4
Procedure
Step L (4): Dichloromethane (20 mL) was added to a flask charged with 3-methoxy-4-(6-methylpyridazin-4-yl)aniline hydrochloride (900 mg, 3.58 mmol) and 1,1′-thiocarbonyldipyridin-2(1H)-one (913 mg, 3.93 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 (0-50% EtOAc/dichloromethane to afford 5-(4-isothiocyanato-2-methoxyphenyl)-3-methylpyridazine (650 mg, 2.53 mmol, 70.7% yield). LC-MS (M+H)+ 258.0. 1H NMR (500 MHz, chloroform-d) δ ppm 9.18 (d, J=2.44 Hz, 1 H) 7.43 (d, J=2.14 Hz, 1 H) 7.32 (d, J=7.93 Hz, 1 H) 6.95 (dd, J=8.09, 1.98 Hz, 1 H) 6.83 (d, J=2.14 Hz, 1 H) 3.85 (s, 3 H) 2.75 (s, 3 H).