Réaction #2275668

Équation de réaction

p-toluenesulfonic acid

4-carboxybenzaldehyde

benzenesulfonamide

toluene

→

4-{[(phenylsulfonyl)imino]methylidene}benzoic acid

Solvants

water

water

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture was then heated
2. 2
   Autrehad separated
3. 3
   Filtrationthe precipitated solid was filtered off
4. 4
   Autredried under vacuum

Mode opératoire

An equimolar mixture of 25.0 g (0.17 mol) 4-carboxybenzaldehyde and 26.7 g (0.17 mol) benzenesulfonamide 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: 45.7 g (94.8%); 1H-NMR (400 MHz, DMSO-d6): δ [ppm]=7.59 (m, 2H); 7.78 (d, 1H); 8.02 (m, 2H); 8.12 (d, 2H); 8.18 (d, 2H); 9.30 (s, 1H); 13C-NMR (400 MHz, DMSO-d6): δ [ppm]=127.8; 129.7; 131.4; 134.1; 135.8; 136.0; 137.9; 166.5; 171.2; 192.9.

Source