Water → HCID 28665340, compound

Participants

Reaction Steps

To a slurry of 2-(4-carboxyphenyl)benzothiazole (4.5 g, 17 mmol.) in DMF (38 mL), potassium carbonate (5.39 g, 39 mmol) was added and the mixture was cooled in an ice bath. Bromoethane (7.2 mL, 102 mmol) was added in portions, and the mixture was allowed to come to room temperature. After 48 hours, the mixture was poured into water and the separated solids (4.51 g) were collected. A solution of the crude product was passed through a column of silica gel. The product residue (4.19 g), left after evaporation of the solvent, was recrystallized from ethanol; 3.96 g (81% yield), m.p. 132-133.6° C. Mass spec: m/z 283 (M+). Anal. Calcd for C16H13NO2S: C, 67.83; H, 4.62; N, 4.94; S, 11.31%. Found, C, 67.86; H, 4.62; N, 4.89; S, 11.45%. FT-IR (KBr; cm−1): 3100 (sp2C—H), 2989 (sp3C—H), 1710 (C═O), 1522 (asym NO2), 1341 (sym NO2), 1279 (C—O—C), 1108, 773, 753, 696. 1H NMR (CDCl3; δ in ppm): 1.45 (t, 3H, methyl), 4.45 (q, 2H, OCH2), 7.4-7.55 (m, 2 ArH), 7.9 (d, 1 ArH), 8.05-8.20 (m, 5 ArH). 13C NMR (CDCl3; δ in ppm): 14.76, 61.72 (sp3 C), 122.12, 123.99, 126.09, 126.99, 127.78, 130.61, 132.79, 135.67, 137.67, 137.74, 154.51, 166.32 (sp2C).

Provenance & Evidence