Ammonia → HCID 10135881, compound

HRID 1178262Notes

Reaction equation

HRID 1178262 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:19][CH2:20][CH2:21][CH2:22][S:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9](Cl)[C:8]=2[N:18]=1)[CH2:2][CH2:3][CH3:4].C(C1[N:35](CCCCSC2C=CC=CC=2)C2C3C=CC=CC=3N=C(SC3C=CC=CC=3)C=2N=1)CCC.N.C>CO.C(OCC)(=O)C>[CH2:1]([C:5]1[N:6]([CH2:19][CH2:20][CH2:21][CH2:22][S:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:35])[C:8]=2[N:18]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 297MethaneHCID 12106187HCID 12106187, compoundHCID 12106188HCID 12106188, compound

Product 1

HCID 10135881HCID 10135881, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A 3:1 mixture of 2-butyl-4-chloro-1-[4-(phenylthio)butyl]-1H-imidazo[4,5-c]quinoline to 2-butyl-4-(phenylthio)-1-[4-(phenylthio)butyl]-1H-imidazo[4,5-c]quinoline (1.38 g) and a solution of 7% ammonia in methanol (30 mL) were combined in a bomb and heated to 150° C. The reaction was judged to be complete after 5 hours. The volatiles were removed under reduced pressure and the resulting residue was stirred in water and made basic (pH 10) with solid sodium carbonate. The aqueous mixture was extracted with chloroform (3×). 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 yellow crystalline solid. The solid (0.8 g) was dissolved in ethyl acetate (50 mL) and brought to reflux. Activated charcoal (0.4 g) was added; the resulting mixture was heated at reflux for 5 minutes and then the charcoal was removed by filtration through fluted paper to provide a colorless solution. The solution was concentrated under reduced pressure to give a solid that was recrystallized from ethyl acetate and hexanes to provide 2-butyl-1-[4-(phenylthio)butyl]-1H-imidazo[4,5-c]quinolin-4-amine (0.51 g, 1.25 mmol) as white needles, m.p. 118-120° C.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. extractionThe aqueous mixture was extracted with chloroform (3×)
  3. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto afford a yellow crystalline solid
  8. temperatureto reflux
  9. temperaturethe resulting mixture was heated
  10. temperatureat reflux for 5 minutes
  11. customthe charcoal was removed by filtration
  12. customto provide a colorless solution
  13. concentrationThe solution was concentrated under reduced pressure
  14. customto give a solid
  15. customthat was recrystallized from ethyl acetate and hexanes

Sources & evidence

ORD record
ord-61c0d771769b4aa9a2645771c9f62ddf
Source dataset
uspto-grants-2007_10
Patent number
US07276515B2

Reaction notes

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