Sodium Hydroxide → HCID 178482588, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-phenylethyl-benzofuran-2-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-methyl-amide (2.29 g, 4.15 mmol), prepared in the previous step, sodium azide (808 mg, 12.4 mmol) and ammonium chloride (668 mg, 12.5 mmol) in 50 mL of DMF was stirred under nitrogen at 100° C. for 5 h. By TLC starting material remained. An additional 801 mg (12.3 mmol) of sodium azide was added and the reaction stirred at 100° C. overnight. The reaction was diluted with 50 mL of 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. An oil precipitated. The aqueous layer was decanted and the oil partitioned between methylene chloride and water. The organic layer was separated, dried (MgSO4) and the solvent removed under reduced pressure to give the title compound as a light brown solid, mp 56-59° C.

Provenance & Evidence