Sodium Hydroxide → HCID 178429305, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-methyl-benzofuran-2-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-methyl-amide (2.039 g, 4.40 mmol), prepared in the previous step, sodium azide (846 mg, 13.0 mmol) and ammonium chloride (695 mg, 13.0 mmol) in 60 mL of DMF was stirred under nitrogen at 100° C. for 6 h. The reaction was diluted with water, made basic by the addition of 1 N NaOH and extracted three times with ethyl acetate. The aqueous layer was acidified with 1 N HCl, which caused an oil to precipitate. The aqueous layer was decanted from the oil. Water was added to the oil, which caused it to solidify. The solid was collected by filtration, rinsed with water and dried under reduced pressure to give the title compound as a white solid, mp 164-166° C.

Provenance & Evidence