2-aminosulfonyl-6-isopropyl-N,N-diethylbenzamide → 4-Isopropylsaccharin
Reaction equation
N[S:2]([C:5]1[CH:17]=[CH:16][CH:15]=[C:14]([CH:18]([CH3:20])[CH3:19])[C:6]=1[C:7]([N:9](CC)CC)=[O:8])(=[O:4])=[O:3]>C(O)(=O)C>[CH:18]([C:14]1[CH:15]=[CH:16][CH:17]=[C:5]2[C:6]=1[C:7](=[O:8])[NH:9][S:2]2(=[O:4])=[O:3])([CH3:20])[CH3:19]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2-aminosulfonyl-6-isopropyl-N,N-diethylbenzamide (60 g) in acetic acid (400 mL) was refluxed for 24 hours, then cooled to room temperature. The solvent was removed under vacuum. The oily residue was dissolved in water (500 mL) and the pH was adjusted to 1 with hydrochloric acid (2N). The crude product was collected by filtration, washed with water (300 mL), dried at 60° C. under vacuum for 18 hours and recrystallized from ether-hexane to give 4-isopropylsaccharin (40 g, 90% yield, m.p. 177° C.).