Sodium Iodide → 6-Chloro-5-fluoro-2,3-dihydro-3-[(2-furoyl)oxy-(2-thienyl)methylene]-2-oxo-1H-indole-1-carboxamide

HRID 326781Notes

Reaction equation

HRID 326781 reaction equation
[Na+].[Cl:2][C:3]1[CH:11]=[C:10]2[C:6](/[C:7](=[C:16](/[OH:22])\[C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)/[C:8](=[O:15])[N:9]2[C:12]([NH-:14])=[O:13])=[CH:5][C:4]=1[F:23].[I-].[Na+].[O:26]1[CH:30]=[CH:29][CH:28]=[C:27]1[C:31](Cl)=[O:32]>ClCCl>[Cl:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7](=[C:16]([O:22][C:31]([C:27]3[O:26][CH:30]=[CH:29][CH:28]=3)=[O:32])[C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)[C:8](=[O:15])[N:9]2[C:12]([NH2:14])=[O:13])=[CH:5][C:4]=1[F:23]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 682422-Furancarbonyl chlorideHCID 178514240HCID 178514240, compound

Product 1

HCID 538322016-Chloro-5-fluoro-2,3-dihydro-3-[(2-furoyl)oxy-(2-thienyl)methylene]-2-oxo-1H-indole-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-36b983ed13464d5a9983b86304ab6a11
Source dataset
uspto-grants-1993_12
Patent number
US05270331

Reaction notes

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