Hydrochloric Acid → HCID 10274459, compound

Participants

Reaction Steps

5-Fluoro-2-methyl-N-[4-bromo-1-naphthyl]benzenesulfonamide—4-Bromo-1-naphthylamine (0.96 g, 4.33 mmol) was dissolved in DCM (10 mL) before pyridine (1 mL) was added. 5-Fluoro-2-methylbenzenesulfonyl chloride was added neat and the reaction mixture was stirred for 16 h. HCl (1 M, 1 mL) was added to the reaction mixture. The organic phase was filtered through a Silica plug using DCM as eluent. The solvent was evaporated. The obtained crude product was purified by flash-chromatography using MeOH (10%) in pentane, to give the desired product as a tar. To increase the purity, the product was purified by recrystallising (EtOAc/hexanes). This gave the product with a purity of 95%. 1H NMR (270 MHz, CDCl3) δ 8.22 (d, J=8.98 Hz, 1H), 7.92 (d, J=7.92 Hz, 1H), 7.64–7.51 (m, 4H), 7.25–7.23 (m, 1H), 7.21–7.05 (m, 2H), 6.84 (br.s, 1H, N—H), 2.55 (s, 3H); MS (ESI+) for C17 H13 Br F N O2 S m/z 394.263 (M+H)+. MS (ESI−) for C17 H13 Br F N O2 S m/z 394.263 m/z (M−H)−.

Provenance & Evidence