m-Chloroperbenzoic acid → HCID 58917312, compound

HRID 547302Notes

Reaction equation

HRID 547302 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH3:12][S:13][CH2:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][N:20]1[C:32]2[C:31]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[N:25]=[C:24]([NH2:33])[C:23]=2[N:22]=[C:21]1[CH2:34][CH2:35][CH3:36]>C(Cl)(Cl)Cl>[CH3:12][S:13]([CH2:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][N:20]1[C:32]2[C:31]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[N:25]=[C:24]([NH2:33])[C:23]=2[N:22]=[C:21]1[CH2:34][CH2:35][CH3:36])=[O:6]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 58917321HCID 58917321, compound

Product 1

HCID 58917312HCID 58917312, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-Chloroperoxybenzoic acid (0.62 g of ˜77%, 2.8 mmol) was added in portions over a period of 5 minutes to a solution of 1-{2-[3-(methylthio)propoxy]ethyl}-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine (1.0 g, 2.8 mmol) in chloroform (14 mL). After 20 minutes analysis by TLC showed that all of the starting material had been consumed. The reaction mixture was partitioned between dichloromethane (100 mL) and saturated aqueous sodium carbonate (50 mL). The organic layer was washed sequentially with saturated aqueous sodium carbonate (50 mL) and brine (50 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to provide a white foam. This material was purified by column chromatography (silica gel eluting with 95/5 dichloromethane/methanol) followed by recrystallization from ethyl acetate (60 mL) to provide 0.44 g of 1-{2-[3-(methylsulfinyl)propoxy]ethyl}-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine as crystalline plates, mp 148-151° C. 1H NMR (300 MHz, DMSO-d6) δ 8.07 (d, J=8.1 Hz, 1H), 7.60 (d, J=8.1 Hz, 1H), 7.40 (t, J=8.1 Hz, 1H), 7.22 (t, J=8.1 Hz, 1H), 6.43 (bs, 2H), 4.72 (t, J=5.0 Hz, 2H), 3.84 (t, J=5.0 Hz, 2H), 3.40 (t, J=6.2 Hz, 2H), 2.92 (t, J=7.6 Hz, 2H), 2.46 (m, 2H), 2.39 (s, 3H) 1.86 (sextet, J=7.6 Hz, 2H) 1.71 pentet, J=7.6 Hz, 2H) 1.04 (t, J=7.6 Hz, 3H); MS (APCI) m/z 375 (M+H)+; Anal. Cacld for C19H26N4O2S: C, 60.94; H, 7.00: N, 14.96. Found: C, 60.73; H, 6.82; N, 14.85.

Workup

  1. customthat all of the starting material had been consumed
  2. customThe reaction mixture was partitioned between dichloromethane (100 mL) and saturated aqueous sodium carbonate (50 mL)
  3. washThe organic layer was washed sequentially with saturated aqueous sodium carbonate (50 mL) and brine (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto provide a white foam
  8. customThis material was purified by column chromatography (silica gel eluting with 95/5 dichloromethane/methanol)
  9. customfollowed by recrystallization from ethyl acetate (60 mL)

Sources & evidence

ORD record
ord-04e1f6767f3143e9b30c90772e45a008
Source dataset
uspto-grants-2011_05
Patent number
US07939526B2

Reaction notes

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