反应详情

To a solution of methyl 2-amino-5-iodothiazole-4-carboxylate (8A) (9 g, 31.7 mmol) in acetonitrile (60 mL) was added CuCl (4.75 g, 48 mmol) followed by t-butyl nitrite (6.19 g, 60 mmol). The mixture was stirred at rt for 2 hours. NH4Cl was then added slowly to the stirring mixture to quench the reaction. The mixture was extracted with EtOAc and the combined extracts were washed with water, brine, dried over Na2SO4, and concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel eluting with 5% EtOAc in hexanes to provide 7.5 g (78%) of the desired product methyl 2-chloro-5-iodothiazole-4-carboxylate (88): LC/MS (APCI): m/z 304.0 (M+H).

1. customto quench
2. customthe reaction
3. extractionThe mixture was extracted with EtOAc
4. washthe combined extracts were washed with water, brine
5. dry with materialdried over Na2SO4
6. concentrationconcentrated under reduced pressure
7. customThe crude material was purified by column chromatography on silica gel eluting with 5% EtOAc in hexanes