Hydrochloric Acid → HCID 178479590, compound

Participants

Reaction Steps

N-(4-Aminophenethyl)benzotriazole-4-sulphonamide (4.53 g, 14 mM) was dissolved in a minimum of boiling ethanol (100 ml). The solution was cooled to -5°, saturated with dry hydrogen chloride and, after further cooling to -10°, amyl nitrite (1.84 g, 16 mM, 2.11 ml) was added over 10 minutes. The mixture was then stirred for 2 hours at -10°. The very small quantity of solid which remained was removed from the reaction mixture by filtration and the filtrate was added, all at once, to a solution of anhydrous stannous chloride (8.13 g, 43 mM) in ethanolic hydrogen chloride (10 ml) at 0°. The reaction mixture was stirred at 0° for 1 hour, left at 5° overnight and then poured into ether (1 liter). The solid which precipitated was collected (4.1 g).

Provenance & Evidence