Thiophenol → HCID 22320547, compound

HRID 432851Notes

Reaction equation

HRID 432851 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:10]([C:14]1[N:15]([CH2:28][CH2:29][CH2:30]Cl)[C:16]2[C:25]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N:19]=[C:18]([NH2:26])[C:17]=2[N:27]=1)[CH2:11][CH2:12][CH3:13]>CN(C)C=O>[CH2:10]([C:14]1[N:15]([CH2:28][CH2:29][CH2:30][S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:16]2[C:25]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N:19]=[C:18]([NH2:26])[C:17]=2[N:27]=1)[CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 24758Sodium hydrideHCID 22320517HCID 22320517, compound

Product 1

HCID 22320547HCID 22320547, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A round bottom flask was charged with a magnetic stir bar, benzenethiol (0.68 g, 6.21 mmol), sodium hydride (0.25 g, 60% dispersion, 6.21 mmol), and anhydrous dimethyl formamide (28 mL) under a nitrogen atmosphere. After the reaction mixture had stirred at ambient temperature for 30 minutes, 2-butyl-1-(3-chloropropyl)-1H-imidazo[4,5-c]quinolin-4-amine (1.64 g, 5.18 mmol) was added and the resulting cloudy solution was heated to 80° C. and maintained at 80° C. for 2.5 hours at which time the starting material was completely consumed. The hot solution was poured into rapidly stirred water (200 mL). The resulting mixture was extracted with chloroform (2×). The combined organic layers were washed with saturated aqueous sodium bicarbonate and brine, dried over anhydrous sodium sulfate, filtered and then concentrated under reduced pressure to afford a light yellow oil. The material was purified by chromatography over silica gel (95/5 dichloromethane/methanol) to provide 2-butyl-1-[3-(phenylthio)propyl]-1H-imidazo[4,5-c]quinolin-4-amine (1.38 g, 3.53 mmol) as a white solid.

Workup

  1. additionA round bottom flask was charged with a magnetic stir bar
  2. temperaturethe resulting cloudy solution was heated to 80° C.
  3. temperaturemaintained at 80° C. for 2.5 hours at which time the starting material
  4. customwas completely consumed
  5. additionThe hot solution was poured into rapidly stirred water (200 mL)
  6. extractionThe resulting mixture was extracted with chloroform (2×)
  7. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate and brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customto afford a light yellow oil
  12. customThe material was purified by chromatography over silica gel (95/5 dichloromethane/methanol)

Sources & evidence

ORD record
ord-4cb02a8162214599af055a19e76f7b8e
Source dataset
uspto-grants-2003_12
Patent number
US06664264B2

Reaction notes

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