Sodium Hydroxide → HCID 178442004, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-butyl-benzofuran-3-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-methyl-amide (0.3 g, 0.59 mmol), prepared in the previous step, sodium azide (0.116 g, 1.78 mmol) and ammonium chloride (0.095 g, 1.78 mmol) in 12 mL DMF was stirred under nitrogen at 100° C. for 6.5 h. The reaction was diluted with water, made basic with 1N NaOH, and extracted three times with ethyl acetate. The organic layers were combined, acidified with 1N HCl, dried (MgSO4) and the solvent removed under reduced pressure to give an oily residue. The oil was diluted with water and the solid that formed was collected by filtration, rinsed with water and dried under reduced pressure to give the title compound (0.20 g, 63%) as an off white solid, mp 190-194° C.

Provenance & Evidence