Water → HCID 16075319, compound

Participants

Reaction Steps

A flask is charged with (3-chlorophenyl)acetic acid (0.34 mmol), 4-dimethylaminopyridine (0.66 mmol), a solution of N-{2-[(E)-hydrazonomethyl]phenyl}-4-(trifluoromethyl)benzenesulfonamide (0.33 mmol) in N,N-dimethylacetamide (1 mL), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.33 mmol). The reaction is stirred at room temperature for 18 hours. The reaction is worked up either by adding water and obtaining a solid precipitate, or by evaporating the reaction mixture. The product is purified on silica gel with ethyl acetate-methylene chloride mixtures. Obtained a 60% yield of N-[2-((E)-{[(3-chlorophenyl)acetyl]hydrazono}methyl)phenyl]-4-(trifluoromethyl)benzenesulfonamide. 1H NMR (400 MHz, CDCl3)(mixture of geometric isomers) d 3.73&4.17(2s, 2H); 7.16 (m); 7.36 (m); 7.47 (s); 7.60m; 7.66 (m); 7.75 (m); 7.89 (s); 7.96 (m); 8.06 (m); 9.62 (bs); 10.80 (bs). ESI− for C22H17ClF3N3O3S: m/z =494 (M−H)−.

Provenance & Evidence