(3,4-Dimethoxyphenyl)acetic acid → HCID 16075323, compound

Participants

Reaction Steps

A flask is charged with (3,4-dimethoxyphenyl)acetic acid (0.34 mmol), 4-dimethylaminopyridine (0.66 mmol), a solution of N-{2-[hydrazonomethyl]phenyl}-N-methyl-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 by evaporating the reaction mixture. The product is purified on silica gel with ethyl acetate-methylene chloride mixtures or methanol-methylene chloride mixtures. A 58% yield of N-[2-((E)-{[(3,4dimethoxyphenyl)acetyl]hydrazono}methyl)phenyl]-N-methyl-4-(trifluoromethyl)benzenesulfonamide is obtained. 1H NMR (400 MHz, CDCl3) (mixture of geometric isomers) d 3.25 (s); 3.90 (2s); 4.10 (m); 6.58 (m); 6.87 (m); 6.96 (m); 7.45 (m); 7.82 (m); 8.20 (m); 8.29 (m); 8.90&8.96 (2bs). ESI− for C25H24F3N3O5S: m/z=534 (M−H)−.

Provenance & Evidence