Pyridine → 4-Acetamidophenyl sulfamate

Participants

Reaction Conditions

Reaction Steps

A reaction flask was charged with 43.8 g (0.252 mole) of sulfamic acid, phenyl ester; 12.6 g (0.084 mole) of 4-acetamidophenol, 9 ml of pyridine and 150 ml p-dioxane. The solution was heated at 75° C. for 18 hours. The solution was concentrated to a brown oil. The oil was portioned between 100 ml methylene chloride and 100 ml of 1.0 N sodium bicarbonate. The mixture was refrigerated overnight then filtered to collect 15.8 g of white solid. 1H NMR spectrum indicated pure product but contaminated with sodium bicarbonate. The solid was added to 100 ml H2O and the mixture stirred for one hour. The solid was collected and dried to give 8.4 g of solid, mp 180°-181° C.

Provenance & Evidence