Benzenesulfonamide → Cyclohexylurea

Participants

Reaction Steps

7.6 g of 4-(β-<1-butyl-1,2-dihydro-2-oxo-nicotinamido>-ethyl)-benzenesulfonamide (melting point 162 - 163° C, prepared from 4-(β-aminoethyl)-benzenesulfonamide and 1-butyl-1,2-dihydro-2-oxo-nicotinic acid chloride in chloroform/soda solution) in 100 ml acetone and 50 ml dioxane were refluxed for 3 hours while stirring together with 5.5 g of pulverized potash. 2.5 g cyclohexyl isocyanate were then added and stirring was continued for 6 hours with reflux. After cooling, the reaction mixture was diluted with water, filtered and the filtrate acidified with 2N hydrochloric acid. The formed precipitate was filtered off with suction, dissolved in dilute ammonia and reprecipitated with dilute hydrochloric acid and finally recrystallized from methanol. The N-[4-(β-<1-butyl-1,2-dihydro-2-oxo-nicotinamido>-ethyl benzenesulfonyl]-N'-cyclohexyl urea obtained melted at 178 - 179° C.

Provenance & Evidence