4-(Benzyloxy)benzene-1-sulfonyl chloride → N-(2,4-dimethylphenyl)-N-(2-methylpropyl)-4-[(phenylmethyl)oxy]benzenesulfonamide
Reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][CH:11]([CH3:13])[CH3:12].[C:14]1([CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>N1C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:10][CH:11]([CH3:13])[CH3:12])[S:28]([C:25]1[CH:24]=[CH:23][C:22]([O:21][CH2:20][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:27][CH:26]=1)(=[O:30])=[O:29]Participants
4
Procedure
To (2,4-dimethylphenyl)(2-methylpropyl)amine (1.00 g, 5.64 mmol) in pyridine (20 mL) was added 4-[(phenylmethyl)oxy]benzenesulfonyl chloride (1.754 g, 6.20 mmol). The reaction mixture was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo then redissolved in ethyl acetate and washed with a 10% solution of citric acid. At this stage a white precipitate formed and was isolated by filtration, LCMS analysis confirmed the precipitate was the desired product. The organic phase was then washed with 2 M NaOH and further precipitate was collected, again confirmed as the desired product by LCMS analysis. The organic phase was dried with magnesium sulfate, concentrated in vacuo and treated with dichloromethane to give a cloudy suspension, which was filtered to provide more of the desired product. Finally the filtrate was concentrated in vacuo and treated with methanol, whereupon additional product crystallised from the solution. The collected batches of product were combined (974 mg, 2.300 mmol) and used without further purification in the next step. LCMS [LCMS1] Rt 1.54 min, m/z (ES+) 424 (M+H).