m-Chloroperbenzoic acid → 2-(2-Diethylaminobenzylsulfinyl)-3-methylquinoxaline
Reaction equation
[CH2:1]([N:3]([CH2:23][CH3:24])[C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1[CH2:6][S:7][C:8]1[C:17]([CH3:18])=[N:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1)[CH3:2].ClC1C=CC=C(C(OO)=[O:33])C=1>C(Cl)(Cl)Cl>[CH2:23]([N:3]([CH2:1][CH3:2])[C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1[CH2:6][S:7]([C:8]1[C:17]([CH3:18])=[N:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1)=[O:33])[CH3:24]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
In 50 ml of chloroform was dissolved 1.7 g of 2-(2-diethylaminobenzylthio)-3-methylquinoxaline. To the chilled solution kept at -10° C. was portionwise added 1.21 g of m-chloroperbenzoic acid (purity: 80%). The reaction liquid was then washed successively with saturated aqueous NaHCO3 solution, water and saturated aqueous sodium chloride solution, and dried over sodium sulfate. The sodium sulfate was then removed by filtration, and the solvent was evaporated under reduced pressure from the filtrate. The residual oil was purified by silica gel column chromatography (hexane/acetone) to give 1.2 g of 2-(2-diethylaminobenzylsulfinyl)-3-methylquinoxaline as a yellow oil.