Dimethyl Sulfoxide → 5,7-Dibromo-6-methoxy-1,3-benzothiazol-2-amine

Participants

Reaction Conditions

Reaction Steps

Anhydrous DMSO (2 mL) was added to a mixture of ethyl N-[(2,3,5-tribromo-4-methoxy-phenyl)carbamothioyl]carbamate (426 mg, 1.02 mmol), CuO (8 mg, 0.10 mmol) and potassium carbonate (211 mg, 1.53 mmol). The mixture was sonicated then heated to 90° C. in a pre-heated heating block under air. The mixture was cooled to rt after 55 minutes and diluted with water. The mixture was extracted into EtOAc (3×50 mL) and the combined organic layers were washed with water then brine. The organic layer was dried over Na2SO4 and the mixture filtered through a PTFE filter to remove copper salts, then the filtrate was concentrated to dryness under reduced pressure. The desired compound was obtained as an off-white solid, 208 mg (60% over 2 steps). m/z: 337.01/339.01/340.97 [M+H]+.

Provenance & Evidence