Sulfuric Acid → HCID 20212201, compound

Participants

Reaction Steps

To a solution of 630 mg (3 mmol) of 9-amino-6-chloro-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine in 2 ml of concentrated sulfuric acid and 10 ml of water was added 280 mg (4 mmol) of sodium nitrate in 5 ml of water. The mixture was stirred in an ice bath during addition, then, allowed to warm to room temperature. After stirring at room temperature for one hour, 60 mg of urea was added to destroy excess nitrous acid. To this solution was added 330 mg (5 mmol) of sodium azide and the resulting solution stirred at room temperature. Nitrogen was evolved and a white precipitate formed. After stirring overnight, this was removed by filtration, stirred with a small amount of cold ethanol, filtered again and washed with ether to leave 545 mg (58%) of slightly off-white crystals, 9-azido-6-chloro-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine sulfate. This material was crystallized from ethanol to give 390 mg as a slightly yellow crystalline solid, m.p. 71°-75° (dec), IR and NMR spectra support structure.

Provenance & Evidence