2-Naphthalenesulfonyl chloride → HCID 9906236, compound

Participants

Reaction Steps

To a stirred solution of the product of step c (437 mg, 1.53 mmol) in ethanol (10 ml) was added hydrazine hydrate (0.37 ml) and the reaction heated at reflux for 1.5 h. The resultant suspension was filtered, the filter-cake was washed with further ethanol (20 ml) and the filtrate was evaporated. The residue was suspended in DCM (20 ml) and the solid was removed by filtration. The filtrate was evaporated at reduced pressure and the residue was dissolved in DCM (5 ml). The solution was treated sequentially, with ice-cooling, with triethylamine (0.290 ml, 2.08 mmol) and 2-naphthalenesulfonyl chloride (217 mg, 1.39 mmol). The coolant was removed and the reaction mixture stirred at ambient temperature for 2 h. The reaction was diluted with DCM (20 ml), washed with water (20 ml) and brine (20 ml), and dried over anhydrous sodium sulfate. The filtrate was evaporated at reduced pressure and the residue was purified by flash column chromatography (90:10:1 DCM:methanol:ammonia) to afford the title compound (240 mg, 45%). 1H NMR 8.44 (1H, d, 1.2), 7.99-7.59 (6H, m), 2.98 (2H, t, 6.9), 2.76-2.69 (2H, m), 2.24 (3H, s), 1.87-1.84 (3H, m), 1.64-1.46 (5H, m), 1.21-1.13 (2H, m), 0.75 (1H, m). Microanalysis found C 64.32 H 7.75 N 7.59. C19H26N2O2S-0.5H2O requires C 64.19 H 7.76 N 7.88.

Provenance & Evidence