Benzenesulfonamide → Cyclohexylurea

Participants

Reaction Steps

2.9 g of 4-(β-<1,2-dihydro-1-methyl-2-oxo-nicotinamido>-ethyl)-benzenesulfonamide (melting point 235 - 237° C, prepared from 4-(β-aminoethyl)-benzenesulfonamide and the mixed anhydride of 1,2-dihydro-1-methyl-2-oxo-nicotinic acid in dilute acetone) in 100 ml acetone/100 ml dioxane were refluxed for 3 hours while stirring together with 2.5 g of pulverized potassium carbonate. 1.4 g of cyclohexyl-isocyanate were then added and the mixture was stirred for 8 hours at boiling temperature. The solvent was distilled off under reduced pressure, water was added to the residue, the whole was filtered, the filtrate acidified, the reaction product was filtered off with suction and recrystallized from dilute ethanol. The N-[4-(β-<1,2 -dihydro-1-methyl-2-oxo-nicotinamido>-ethyl)-benzenesulfonyl]N'-cyclohexyl urea obtained melted at 210 - 212° C.

Provenance & Evidence