Water → 2-Chloro-4-(4-(3-(4-fluoro-3-methoxyphenyl)thioureido)-2-methyl-3-oxobutan-2-yl)benzenesulfonamide

Participants

Reaction Steps

To a stirred mixture of 4-(4-amino-2-methyl-3-oxobutan-2-yl)-2-chlorobenzenesulfonamide hydrochloride (7.8 g, 23.7 mmol) in DCM (150 mL) was added Et3N (9.9 mL, 71.1 mmol, 3 eq) and 1-fluoro-4-isothiocyanato-2-methoxybenzene (4.35 g, 23.7 mmol). After stirring 2 h, DCM and water were added to the reaction mixture. The organic layer was separated, dried over MgSO4 and evaporated in vacuo. The residue was purified by flash column chromatography (Hex/EtOAc=1:1 to EtOAc/DCM=1:1) to give 2-chloro-4-(4-(3-(4-fluoro-3-methoxyphenyl)thioureido)-2-methyl-3-oxobutan-2-yl)benzenesulfonamide (8.6 g, 76%). 1H NMR (400 MHz, CDCl3) δ 8.08 (d, J=8.4 Hz, 1H), 7.80 (s, 1H), 7.43 (d, J=2.0 Hz, 1H), 7.30 (d, J=8.8 Hz, 1H), 7.15 (m, 1H), 6.89 (d, J=7.6 Hz, 1H), 6.77 (m, 2H), 5.30 (s, 2H), 4.43 (d, J=4.4 Hz, 2H), 3.91 (s, 3H), 1.59 (s, 6H).

Provenance & Evidence