3-Aminobenzenesulfonic acid → 3-(4-Tert-butylbenzamido)benzenesulfonic acid
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([S:8]([OH:11])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[C:12]([C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13]>N1C=CC=CC=1>[C:12]([C:16]1[CH:17]=[CH:18][C:19]([C:20]([NH:1][C:2]2[CH:3]=[C:4]([S:8]([OH:11])(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=2)=[O:21])=[CH:23][CH:24]=1)([CH3:15])([CH3:13])[CH3:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3-amino benzenesulfonic acid (1.7 g, 10 mmol) in pyridine (100 mL) was added 4-tert-butyl benzoyl chloride (2.0 mL, 10 mmol). The reaction was stirred at room temperature 16 h and the solvent was evaporated under vacuum. The residue was dissolved in EtOAc and washed with 1 M aqueous hydrochloric acid. The aqueous washes were extracted with EtOAc. The combined organic extracts were dried over Na2SO4 and concentrated under vacuum. The residue was purified by silica gel chromatography (10%-20% MeOH—CH2Cl2) to obtain 3-(4-tert-butylbenzamido)benzenesulfonic acid (2.1 g, 63% yield). LC/MS: m/z 334.3 (M+H)+ at 2.79 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).