N-Methyl-p-toluenesulfonamide → 2,4-Dimethylbenzenesulfonamide
Reaction equation
C[NH:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)(=[O:5])=[O:4].[CH3:13]C1C=CC(C(Cl)=O)=CC=1>C1(C)C(C)=CC=CC=1>[CH3:13][C:7]1[CH:8]=[C:9]([CH3:12])[CH:10]=[CH:11][C:6]=1[S:3]([NH2:2])(=[O:5])=[O:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
N-Methyl-4-methylbenzene sulfonamide (3.70 g, 0.02 mol) and 4-methylbenzoyl chloride (3.08 g, 0.02 mol) were dissolved in xylene and refluxed for 72 hrs. After evaporation of the xylene, the residue was dissolved in ethyl acetate and washed with dilute sodium carbonate solution. After separation, drying over anhydrous magnesium sulfate and evaporation of the solvent in vacuo, the residue was recrystallized from hexane-ethyl acetate to give N-4-methylbenzoyl-N*-methyl-4-methylbenzene sulfonamide mp 90–92° C. MS m/z 303. (M+ calcd for C16H17NO3S=303). H NMR (300 Mhz, CDCl3) d 2.30 (s, 3, CH3), 2.46 (s, 3, CH3), 7.21 (m, 2, aromatic), 7.35 (m, 2, aromatic), 7.49 (m, 2, aromatic), 7.84 (m, 2, aromatic).