Water → (2-Butyl-5-methylsulfanylamino-benzofuran-3-yl)-[4-(3-dibutylamino-propoxy)-phenyl]-methanone

Participants

Reaction Steps

1.98 g of methanesulfenyl chloride (II) (0.024 mol, 1.2 eq; freshly prepared as described in the above mentioned literature), 9.57 g of (5-amino-2-butyl-benzofuran-3-yl)-[4-(3-dibutylamino-propoxy)-phenyl]-methanone (III) (0.02 mol, 1 eq) and 10 mL of 1.5 M sodium methylate methanolic solution were added into a flask and the mixture was diluted with 50 mL of methanol. The reaction mixture was stirred for 3 hours at room temperature. After the reaction was complete (followed by HPLC) the mixture was poured into 150 mL of water. The product was extracted with 2×60 mL of dichloromethane. The organic phase was washed with 50 mL of aq. NaHCO3 solution and then with 50 mL of water. The solvent was evaporated and the product was purified by column chromatography (column: spheric silica (60 Å); eluent: toluene:MTBE:methanol=50:40:10) to obtain 9.14 g of compound (IV) (87%) as a light yellow oil.

Provenance & Evidence