2-Naphthalenesulfonyl chloride → HCID 15388896, compound

Participants

Reaction Steps

To 1.0 g of methyl 3-aminobenzoate (6) (6.62 mmol) in 10 mL of tetrahydrofuran containing 2 mL (14.4 mmol) of triethylamine was added 1.58 g (6.96 mmol) of 2-napthalenesulfonyl chloride. After 10 min, 100 mg of N,N-dimethylaminopyridine was added. After 15 min, another 600 mg of 2-napthalenesulfonyl chloride was added. After stirring for 30 min, the reaction mixture was quenched with 2N HCl and then extracted into ether. The ethereal phase was washed sequentially with water and saturated NaHCO3, then dried (MgSO4), concentrated, and triturated with ether/petroleum ether to give 2.6 g of the title compound as a colorless powder: 1H-NMR (CDCl3, 200 MHz) δ8.46 (s, 2H), 8.13 (d, 1H, J=7.8 Hz), 7.92-8.04 m, 8H), 7.59-7.75 (m, 5H), 7.42 (t, 1H, J=8 Hz), 7.22 (d, 1H, J=7.6 Hz), 3.80 (s, 3H).

Provenance & Evidence