4-Toluenesulfonyl chloride → HCID 66813869, Verbindung
Reaktionsgleichung
ClC1C=C(C=CC=1)C(OO)=O.[CH2:12]([N:19]1[C:31]2[C:30]3[CH:29]=[CH:28][C:27]([Br:32])=[CH:26][C:25]=3[N:24]=[CH:23][C:22]=2[N:21]=[C:20]1[NH2:33])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[OH-].[NH4+:46]>>[CH2:12]([N:19]1[C:31]2[C:30]3[CH:29]=[CH:28][C:27]([Br:32])=[CH:26][C:25]=3[N:24]=[C:23]([NH2:46])[C:22]=2[N:21]=[C:20]1[NH2:33])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1Komponenten
5
Versuchsvorschrift
3-Chloroperoxybenzoic acid (3.7 g of approximately 77% pure material) was added to a solution of 1-benzyl-7-bromo-1H-imidazo[4,5-c]quinolin-2-amine (2.91 g, 8.24 mmol), and the reaction was stirred for two hours at room temperature. Concentrated aqueous ammonium hydroxide (50 mL) and p-toluenesulfonyl chloride (3.1 g, 16 mmol) were added, and the mixture was stirred overnight at room temperature. The organic layer was separated and washed with water (3×200 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product (1.88 g) was purified by automated flash chromatography (silica cartridge, eluting with aqueous ammonium hydroxide:methanol:dichloromethane in a gradient from 0:0:100 to 0.55:10.45:89) to provide 123 g of 1-benzyl-7-bromo-1H-imidazo[4,5-c]quinolin-2,4-diamine as a reddish-brown solid.