HCID 135727397, compound → HCID 135727395, compound

Participants

Reaction Steps

A solution of 3.47 g (0.0050 mole) 4-(N,N-didodecylsulfamyl)-2-(p-methoxyphenylazo)-1-naphthol in 50 ml tetrahydrofuran containing 0.5 g 5% palladium/carbon catalyst was hydrogenated at low pressure and room temperature for 2 hr. The mixture was filtered and poured into water, then extracted with ether. The extract was concentrated to a gum which was dissolved in 50 ml pyridine. The solution was cooled in an ice bath, and 2.17 g (0.005 mole) 4-acetamido-5-hydroxy-6-(o-methoxyphenylazo)naphthalene-1-sulfonyl chloride was added. The mixture was stirred overnight at room temperature, then poured into ice-water containing 50 ml concentrated hydrochloric acid. The purple solid was recrystallized from dichloroethane and ethyl acetate to give, after drying under vacuum, an amorphous solid (Compound No. 14), m.p. 200°-202° C.

Provenance & Evidence