Thioacetamide → 2-Methyl-5,6-dihydrobenzo[d]thiazol-7(4H)-one

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-bromocyclohexane-1,3-dione (8 g, 42 mmol) in pyridine (50 mL), was added thioacetamide (3.2 g, 42.5 mmol). The reaction mixture was heated at 100° C. for 16 hours. The solvent was then removed under reduced pressure the residue poured in water (250 mL). The reaction mixture was extracted with dichloromethane (3×100 mL). The organic extract was dried using anhydrous sodium sulfate, concentrated under reduced pressure. The crude product was purified by flash column chromatography (Silica gel, gradient from 100% dichloromethane to 2% methanol in dichloromethane) to give the pure desired product (3 g, 42%) as a solid. 1H NMR (CDCl3, 400 MHz): δ 3.01 (t, J=6.0 Hz, 2H), 2.74 (s, 3H), 2.60 (t, J=4 Hz, 2H), 2.20 (quintet, J=4 Hz, 2H); LCMS [M+H]: 168.

Provenance & Evidence