Iodine → HCID 14281027, compound

HRID 867490Notes

Reaction equation

HRID 867490 reaction equation
[CH:1]1([N:7]2[C:11]([CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]3[CH:18]=[CH:19][C:20]([N+:31]([O-])=O)=[C:21]([CH:23]=[C:24]4[NH:28][C:27](=[O:29])[NH:26][C:25]4=O)[CH:22]=3)=[N:10][N:9]=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.II>CN(C)C=O.[Pd]>[CH:1]1([N:7]2[C:11]([CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]3[CH:18]=[CH:19][C:20]4[N:31]=[C:25]5[NH:26][C:27](=[O:29])[NH:28][C:24]5=[CH:23][C:21]=4[CH:22]=3)=[N:10][N:9]=[N:8]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 807IodineHCID 54085014HCID 54085014, compound

Product 1

HCID 14281027HCID 14281027, compoundYield 20.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-[[5-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-2-nitrophenyl]methylene-2,4-imidazolidinedione (12 g, 26 mmol) in dimethylformamide (200 mL) was hydrogenated at 55 p.s.i. over 10% palladium on charcoal (1.2 g) in a low pressure hydrogenation apparatus. After 40 hours, the mixture was filtered through kieselguhr, the solvent evaporated and the residue suspended in refluxing methanol. Iodine (6.69 g, 26 mmol) was added portionwise over 4 minutes, reflux continued for 10 minutes, and the mixture then concentrated in vacuo to approximately 70 mL. 10% Sodium thiosulate solution and 10% sodium carbonate solution was added, the mixture stirred for 5 minutes and a solid filtered off, washed with water and dried in air. This was dissolved in hot dimethylformamide and water added to precipitate a solid (4.80 g) which was dissolved in 10% hydrogen chloride in methanol. The methanol was removed and the residue crystallized from ethanol to give the hydrochloride salt of 7-[4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy]-1,3-dihydro-2H-imidazo[4,5-b]quinolin-2-one (2.16 g, 18% overall), m.p. 288°-291° C.

Workup

  1. filtrationthe mixture was filtered through kieselguhr
  2. customthe solvent evaporated
  3. temperaturein refluxing methanol
  4. temperaturereflux
  5. waitcontinued for 10 minutes
  6. concentrationthe mixture then concentrated in vacuo to approximately 70 mL
  7. addition10% Sodium thiosulate solution and 10% sodium carbonate solution was added
  8. filtrationa solid filtered off
  9. washwashed with water
  10. customdried in air
  11. dissolutionThis was dissolved in hot dimethylformamide
  12. additionwater added
  13. customto precipitate a solid (4.80 g) which
  14. dissolutionwas dissolved in 10% hydrogen chloride in methanol
  15. customThe methanol was removed
  16. customthe residue crystallized from ethanol

Sources & evidence

ORD record
ord-5c94306c3de24194938211dfd126ec0b
Source dataset
uspto-grants-1988_10
Patent number
US04775674

Reaction notes

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