Bromine → HCID 86633157, compound

Participants

Reaction Steps

A solution of bromine in dichloromethane (3.4 mL, 1.0M in DCM, 1.0 eq) was added dropwise to a solution of (5-methyl-2-trifluoromethylphenyl)-thiourea (800 mg, 3.4 mmol, 1.0 eq) in dry DCM (100 mL) below 30° C. The reaction mixture was heated at reflux for 3 h and cooled to room temp. A precipitate was collected by filtration, then suspended in water (20 mL), and the pH was adjusted to 11 with NH4OH. The mixture was then extracted with ethyl acetate (3×20 mL), and the combined organic layers were washed with water (30 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The brown residue was purified by column chromatography on silica gel (eluted by 1% methanol in DCM) to afford 2-amino-7-methyl-4-trifluoromethyl-1,3-benzothiozole as white solid. 1H-NMR (CDCl3, 300 MHz): δ=7.53 (d, J=8.4, 1H), 7.15 (d, J=8.4, 1H), 5.76 (brs, 2H), 2.59 (s, 3H).

Provenance & Evidence