2-Thiophenesulfonyl chloride → N-(4-hydroxynaphthalen-1-yl)thiophene-2-sulfonamide

Participants

Reaction Steps

1.957 g 4-aminonaphth-1-ol hydrochloride salt was suspended in 80 ml dichloromethylene, to which at 0° C. was added 3.0 ml triethylamine. The suspension became a dark brown solution. To the solution was added 1.827 g thiophene-2-sulfonyl chloride. The mixture was stirred at r.t. overnight. The reaction mixture was diluted with dichloromethylene to 200 ml and washed with 1N HCl solution (30 ml×3), water (30 ml×3) and brine (30 ml). Dried over MgSO4, the organic phase was filtered and the filtrate was concentrated to dryness. The crude product was suspended in 50% methanol/H2O and filtered. The solid was washed with 50% methanol/H2O affording 2.7 g (90%) brown solid, m.p.: 146-148° C.

Provenance & Evidence