Toluene → 4-{[(4-Chlorobenzene-1-sulfonyl)imino]methyl}benzoic acid

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Reaction Steps

An equimolar mixture of 25.0 g (0.17 mol) 4-carboxybenzaldehyde and 32.6 g (0.17 mol) 4-chlorobenzenesulfonamide was placed into toluene. 100 mg p-toluenesulfonic acid was added as a catalyst. The mixture was then heated under reflux on a water separator until the theoretically calculated quantity of water had separated. After cooling to room temperature, the precipitated solid was filtered off and dried under vacuum. Yield: 48.3 g (89.4%); 1H-NMR (400 MHz, DMSO-d6): δ [ppm]=7.78 (d, 2H); 8.09 (d, 2H); 8.11 (d, 2H); 8.23 (d, 2H); 9.29 (s, 1H); 13C-NMR (400 MHz, DMSO-d6): δ [ppm]=130.2; 130.5; 131.8; 135.5; 136.0; 136.1; 139.1; 166.6; 171.9; 193.0.

Provenance & Evidence