Sodium Hydroxide → HCID 72187842, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(ethylsulfinyl)-6-methyl-4-morpholin-4-yl-benzamide (0.17 g, 0.57 mmol) in benzene-tetrahydrofuran (1:1) (8 ml) are added tetrabutylammonium hydrogensulfate (0.02 g, 0.057 mmol) and 15% sodium hydroxide solution (5 ml) at RT. 4-Chlorobenzyl bromide (0.083 g, 0.40 mmol) in tetrahydrofuran (0.5 ml) is added and the reaction mixture is slowly heated to 70° C. The reaction mixture is stirred at 70° C. for additional 25 min. After completion of the reaction (monitored by TLC), the organic layer is separated and the aqueous layer is extracted with ethyl acetate (2×20 ml). The organic layer is washed with water (20 ml), brine (20 ml), dried over anhydrous sodium sulfate and evaporated to get the crude product, which is purified by column chromatography (silica gel, 20% acetone/hexane) to yield N-[(4-chlorophenyl)-methyl]-2-(ethylsulfinyl)-6-methyl-4-morpholin-4-yl-benzamide (example 6) (0.12 g, 0.28 mmol, 50%). [M+H]+ 421.1.

Provenance & Evidence