反应详情

To a solution of methyl 4-amino-3-phenylisothiazole-5-carboxylate (Preparation 103C, 700 mg, 2.99 mmol) in chloroform (80 mL) were added iodine (4019 mg, 15.84 mmol) and amyl nitrite (0.602 mL, 4.48 mmol). The resulting mixture was heated to reflux for 30 min. The reaction mixture was cooled to room temperature and washed with aqueous sodium thiosulfate and then water. The organic layer was dried over sodium sulfate. Removal of the solvent in vacuo and crystallization from ethanol yielded methyl 4-iodo-3-phenylisothiazole-5-carboxylate (600 mg, 1.738 mmol, 58.2% yield) as a pale yellow solid. The compound had an LC/MS M+1=346.0.

1. temperatureThe resulting mixture was heated
2. temperatureto reflux for 30 min
3. washwashed with aqueous sodium thiosulfate
4. dry with materialThe organic layer was dried over sodium sulfate
5. customRemoval of the solvent
6. customin vacuo and crystallization from ethanol