Iodine → Bmy 21638

HRID 867489Notes

Reaction equation

HRID 867489 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])=[CH:6][C:5]=1[CH:24]=[C:25]1[NH:29][C:28](=[O:30])[NH:27][C:26]1=O)([O-])=O.II>CN(C)C=O.[Pd].S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+]>[C:18]1([S:15]([CH2:14][CH2:13][CH2:12][CH2:11][O:10][C:7]2[CH:8]=[CH:9][C:4]3[N:1]=[C:26]4[NH:27][C:28](=[O:30])[NH:29][C:25]4=[CH:24][C:5]=3[CH:6]=2)(=[O:17])=[O:16])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 2

HCID 807IodineHCID 53986966HCID 53986966, compound

Product 1

HCID 5492386Bmy 21638

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 11430Potassium CarbonateSolventHCID 24477Sodium ThiosulfateSolvent

Procedure

A solution of 5-[[2-nitro-5-[4-(phenylsulfonyl)butoxy]phenyl]methylene]-2,4-imidazolidinedione (4.12 g, 9.1 mmol) in dimethylformamide (125 mL) was hydrogenated at 60 p.s.i. over 10% palladium on charcoal (1.25 g) in a low pressure hydrogenation apparatus. After 18 hours, the mixture was filtered through kieselguhr, the solvent evaporated and the residue dissolved in dimethylformamide (125 mL) and resubjected to hydrogenation over 10% palladium on charcoal (1.2 g). After 4 hours, the mixture was filtered through kieselguhr, concentrated in vacuo and the residue dissolved in refluxing methanol (150 mL). Iodine (2.35 g, 9 mmol) was added and the mixture refluxed for 1 hour, cooled and diluted with 10% sodium thiosulfate solution and 10% potassium carbonate solution. The mixture was stirred for 10 minutes, filtered and the solid washed with water and dried at 90° C. in vacuo. Crystallization from acetonitrile/dimethylformamide/water afforded 7-[4-(phenylsulfonyl)butoxy]-1,3-dihydro-2H-imidazo[4,5-b]quinolin-2-one as a partial hydrate (1.90 g, 51%), m.p. 258° C. (dec.).

Workup

  1. filtrationthe mixture was filtered through kieselguhr
  2. customthe solvent evaporated
  3. dissolutionthe residue dissolved in dimethylformamide (125 mL)
  4. waitAfter 4 hours
  5. filtrationthe mixture was filtered through kieselguhr
  6. concentrationconcentrated in vacuo
  7. dissolutionthe residue dissolved
  8. temperaturein refluxing methanol (150 mL)
  9. temperaturethe mixture refluxed for 1 hour
  10. temperaturecooled
  11. filtrationfiltered
  12. washthe solid washed with water
  13. customdried at 90° C. in vacuo
  14. customCrystallization from acetonitrile/dimethylformamide/water

Sources & evidence

ORD record
ord-676baf62e5834888baa2d5523ae89e40
Source dataset
uspto-grants-1988_10
Patent number
US04775674

Reaction notes

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