反应详情

To a stirred suspension of (Z)- 6-chloro-5-fluoro-2,3-dihydro-3-(hydroxy-2-thienylmethylene)-2-oxo-1H-indole-1-carboxamide sodium salt (1.4 gm., 3.88 mmole) and sodium iodide (20 mg, 0.12 mmole) in 30 ml of dichloromethane was added 2-furoyl chloride (380 mg, 3.88 mmole). The resulting suspension was then stirred for 20 hr. at room temperature. The reaction suspension was filtered and washed with dichloromethane to remove unreacted 6-chloro-5-fluoro-2,3-dihydro-3-(hydroxy-2-thienylmethylene)-2-oxo-1H indole-1-carboxamide sodium salt. The filtrate was evaporated in vacuo to an orange solid which was chromatographed on a silica gel column (100 gm. silica gel) and eluted with dichloromethane to yield the crude titled compound as a solid. The solid was crystallized from dichloromethane and hexane to yield a yellow solid, 210 mg (12.6%): mp 215°-216° C. Anal. calcd. for C19H10ClFN2O5S: C, 52.73; H, 2.33; N, 6.47. Found: C, 52.66; H, 2.21; N, 6.46.

1. customat room temperature
2. filtrationThe reaction suspension was filtered
3. washwashed with dichloromethane
4. customto remove unreacted 6-chloro-5-fluoro-2,3-dihydro-3-(hydroxy-2-thienylmethylene)-2-oxo-1H indole-1-carboxamide sodium salt
5. customThe filtrate was evaporated in vacuo to an orange solid which
6. customwas chromatographed on a silica gel column (100 gm. silica gel)
7. washeluted with dichloromethane