Potassium Iodide → HCID 53794227, compound

HRID 893574Notes

Reaction equation

HRID 893574 reaction equation
Br[CH:2](Br)[CH3:3].[I-].[K+].C(=O)([O-])[O-].[K+].[K+].[Cl:13][C:14]1[C:15]([F:32])=[C:16]([F:31])[CH:17]=[C:18]2[C:23]=1[N:22]=[C:21]([SH:24])[C:20]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:19]2[OH:30]>CN(C)C=O>[Cl:13][C:14]1[C:15]([F:32])=[C:16]([F:31])[CH:17]=[C:18]2[C:23]=1[N:22]1[CH:2]([CH3:3])[S:24][C:21]1=[C:20]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:19]2=[O:30]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 112011,1-DibromoethaneHCID 11430Potassium CarbonateHCID 178470130HCID 178470130, compound

Product 1

HCID 53794227HCID 53794227, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 13.7 g of 1,1-dibromoethane, 5.7 g of potassium iodide and 9.5 g of potassium carbonate in 60 ml of N,N-dimethylformamide, a solution of 11.1 g of ethyl 8-chloro-6,7-difluoro-4-hydroxy-2-mercaptoquinoline-3-carboxylate in 240 ml of N,N-dimethylformamide was added dropwise at from 110° C. to 115° C. during 2 hours with stirring. After stirring for 30 minutes at the same temperature, the reaction mixture was concentrated in vacuo and water was added to the residue. The precipitate was collected by filtration and chromatographed on silica gel using chloroform. The eluent was recrystallized from a mixture of chloroform and diethyl ether to give colorless needles, m.p. 191°-194° C.

Workup

  1. stirringAfter stirring for 30 minutes at the same temperature
  2. concentrationthe reaction mixture was concentrated in vacuo and water
  3. additionwas added to the residue
  4. filtrationThe precipitate was collected by filtration
  5. customchromatographed on silica gel
  6. customThe eluent was recrystallized from a mixture of chloroform and diethyl ether
  7. customto give colorless needles, m.p. 191°-194° C.

Sources & evidence

ORD record
ord-602cebf8b1324cbcbd26455244242ecd
Source dataset
uspto-grants-1992_06
Patent number
US05126337

Reaction notes

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