Sodium methanethiolate → HCID 9819438, compound

HRID 1182226Notes

Reaction equation

HRID 1182226 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:19][CH2:20][CH2:21][CH2:22]Cl)[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:17])[C:8]=2[N:18]=1)[CH2:2][CH2:3][CH3:4].[CH3:24][S-:25].[Na+]>CN(C)C=O>[CH2:1]([C:5]1[N:6]([CH2:19][CH2:20][CH2:21][CH2:22][S:25][CH3:24])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:17])[C:8]=2[N:18]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 22320426HCID 22320426, compound

Product 1

HCID 9819438HCID 9819438, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A round bottom flask was charged with a magnetic stir bar, 2-butyl-1-(4-chlorobutyl)-1H-imidazo[4,5-c]quinolin-4-amine (1.5 g, 4.53 mmol), sodium thiomethoxide (0.48 g, 6.80 mmol), and anhydrous dimethyl formamide (18 mL) under a nitrogen atmosphere. The reaction mixture was heated to 60° C. to give a homogeneous solution that was maintained at 60° C. for 16 hours at which time the starting material was completely consumed. The solution was cooled and then partitioned between chloroform and water. The layers were separated and the organic layer was washed with saturated aqueous sodium bicarbonate. The combined aqueous layers were extracted with chloroform (1×). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and then concentrated under reduced pressure to afford a dark brown oil. The material was purified by chromatography over silica gel (90/10 dichloromethane/methanol) to provide a light yellow solid. The solid was recrystallized from dimethyl formamide and water to give 2-butyl-1-[4-(methylthio)butyl]-1H-imidazo[4,5-c]quinolin-4-amine (0.83 g, 2.42 mmol) as light yellow needles, m.p. 127–130° C.

Workup

  1. additionA round bottom flask was charged with a magnetic stir bar
  2. customto give a homogeneous solution that
  3. temperaturewas maintained at 60° C. for 16 hours at which time the starting material
  4. customwas completely consumed
  5. temperatureThe solution was cooled
  6. custompartitioned between chloroform and water
  7. customThe layers were separated
  8. washthe organic layer was washed with saturated aqueous sodium bicarbonate
  9. extractionThe combined aqueous layers were extracted with chloroform (1×)
  10. washThe combined organic layers were washed with brine
  11. dry with materialdried over anhydrous sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure
  14. customto afford a dark brown oil
  15. customThe material was purified by chromatography over silica gel (90/10 dichloromethane/methanol)
  16. customto provide a light yellow solid
  17. customThe solid was recrystallized from dimethyl formamide and water

Sources & evidence

ORD record
ord-65d582aa0d5646ac9e90e12aa5e4a4d1
Source dataset
uspto-grants-2007_10
Patent number
US07288550B2

Reaction notes

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