m-Chloroperbenzoic acid → 2-butyl-1-{2-[2-(methylsulfonyl)ethoxy]ethyl}-1H-imidazo[4,5-c]quinoline 5-oxide
Reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH2:12]([C:16]1[N:17]([CH2:29][CH2:30][O:31][CH2:32][CH2:33][S:34]([CH3:37])(=[O:36])=[O:35])[C:18]2[C:27]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N:21]=[CH:20][C:19]=2[N:28]=1)[CH2:13][CH2:14][CH3:15]>C(Cl)(Cl)Cl>[CH2:12]([C:16]1[N:17]([CH2:29][CH2:30][O:31][CH2:32][CH2:33][S:34]([CH3:37])(=[O:36])=[O:35])[C:18]2[C:27]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N+:21]([O-:6])=[CH:20][C:19]=2[N:28]=1)[CH2:13][CH2:14][CH3:15]Participants
Procedure
Solid 3-chloroperoxybenzoic acid (2.1 g of ˜60%) was added in portions over a period of 3 minutes to a solution of 2-butyl-1-{2-[2-(methylsulfonyl)ethoxy]ethyl}-1H-imidazo[4,5-c]quinoline (2.7 g, 7.2 mmol) in chloroform (72 μL). The reaction mixture was stirred at ambient temperature for 30 minutes then additional 3-chloroperoxybenzoic acid (0.4 g) was added. The reaction mixture was stirred at ambient temperature for 15 minutes and then 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 then concentrated under reduced pressure to provide 2-butyl-1-{2-[2-(methylsulfonyl)ethoxy]ethyl}-1H-imidazo[4,5-c]quinoline 5-oxide as an orange foam.
Workup
- stirringThe reaction mixture was stirred at ambient temperature for 15 minutes
- custompartitioned between dichloromethane (100 mL) and saturated aqueous sodium carbonate (50 mL)
- washThe organic layer was washed sequentially with saturated aqueous sodium carbonate (50 mL) and brine (50 mL)
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-89708cfacac24778abb892d372d0c31c
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07939526B2
Reaction notes
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