Sodium Hydroxide → HCID 178441201, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-butyl-benzofuran-2-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-methyl-amide (1.90 g, 3.77 mmol), prepared in the previous step, sodium azide (735 mg, 11.3 mmol) and ammonium chloride (607 mg, 11.3 mmol) in 50 mL of DMF was stirred under nitrogen at 100° C. for 5 h. By TLC starting material remained. An additional 732 mg (11.3 mmol) of sodium azide was added and the stirring continued at 100° C. for 2 h. The reaction was diluted with 50 mL of water, made basic by the addition of 1 N NaOH and then extracted three times with ethyl acetate. The aqueous layer was acidified with 1 N HCl and the solid that formed was collected by filtration and dried under reduced pressure to give the title compound (1.17 g, 57%) as a light brown solid, mp 180-183° C.

Provenance & Evidence