Chlorotrimethylsilane → 2-(4-Bromophenyl)benzothiazole

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-bromobenzoyl chloride (3.0 g, 24 mmol), 2-aminobenzenethiol (4.44 g, 24 mmol) and TMSCl (6.52 g, 60 mmol) in DMF (45 mL) was heated at about 90° C. overnight under argon. The mixture was poured into ice (300 g), and the whole was sonicated for about 20 min and yellow precipitate formed. After filtration, the solid were collected and dissolved in dichloromethane, then washed with aqueous NaHCO3 (150 mL), water (150 mL) and brine (100 mL). The organic phase was dried over Na2SO4, loaded on silica gel, and purified by flash chromatography (hexanes/ethyl acetate 20:1). The fraction one was collected and concentrated and white solid (16) was obtained (2.89 g, 42% yield).

Provenance & Evidence