Iodine → Methyl 4-iodo-3-phenylisothiazole-5-carboxylate

Participants

Reaction Steps

To a solution of methyl 4-amino-3-phenylisothiazole-5-carboxylate (500 mg, 2.134 mmol) in chloroform (15 mL) was added iodine (287 mg, 11.31 mmol) and amyl nitrite (0.430 mL, 3.20 mmol). The resulting mixture was heated at reflux for 30 min., cooled to room temperature, washed with aqueous sodium thiosulfate and water. The organic layer was dried over Na2SO4. Removal of the solvent in vacuo and crystallization from ethanol yielded methyl 4-iodo-3-phenylisothiazole-5-carboxylate (300 mg, 0.869 mmol, 40.7% yield) as a pale yellow solid.

Provenance & Evidence