Acetonitrile → Benzenamine, 2-(tetradecyloxy)-

Participants

Reaction Conditions

Reaction Steps

2-Myristyloxybenzohydroxamic acid was synthesized according to the method provided in part (i) of Example 1. Thereafter, one gram of said compound was dissolved in 5 ml of tetrahydrofuran, and thereto were added 0.83 ml of sodium methylate (28 wt % methanol solution) and 20 ml of acetonitrile. The mixture was heated to 60° C. and kept there for 1.5 hours with stirring (the formation rate of the desired compound in this reaction system was found to be 100% by an analysis using high-speed liquid chromatography). The resulting solution was admixed with 50 ml of ethyl acetate, and washed once with 50 ml of saturated brine and then twice with water. The organic layer was separated from the aqueous layer, dried with Glauber's salt, and then concentrated. The residue was admixed with 5 ml of methanol, and cooled in an ice bath to precipitate white crystals. These white crystals were filtered off, washed with 0.5 ml of ice-cold methanol, and then dried. Thus, 400 mg of 2-myristyloxyaniline (Compound 3) was obtained in a 67% yield. The melting point thereof was 45.5°-46.5° C.

Provenance & Evidence