Sodium Azide → HCID 11037520, compound

Participants

Reaction Steps

N-Bromosuccinimide (NBS, 350 mg, 1.96 mmol) was added in aliquots to a precooled (−5° C.) suspension prepared by mixing a solution of 3 (61 mg, 1.95 mmol) in 1,2-dimethoxyethane (25 ml) with a solution of sodium azide (510 mg, 7.84 mmol) in water (1.2 ml). The initial yellow color faded away after each addition. When all the NBS was consumed, the reaction mixture was allowed to stand at 0° C. for 30 min., prior to pouring onto ice-water (25 ml), and extraction with dichloromethane (3×50 ml). The dichloromethane extract was washed with cold water (25 ml), dried (Na2SO4), the solvent was removed in vacuo to yield a residue which was purified by elution from a silica gel column using chloroform:methanol (98:2, v/v) as eluent to yield 4 (388 mg, 45.5%) as a viscous oil which was used in the next reaction.

Provenance & Evidence