Anthranilic Acid → 2-(Octadecanoylamino)benzoic acid

Participants

Reaction Conditions

Reaction Steps

Triethylamine (0.46 ml) was added to a suspension of stearic acid (853 mg) in methylene chloride (8.5 ml). Then, ethyl chlorocarbonate (0.32 ml) was dropwise added to the mixture while being cooled with ice. After being stirred for 1 hour at 0° C., the mixture, with a solution of anthranilic acid (411 mg) and triethylamine (0.42 ml) in methylene chloride (2 ml) dropwise added thereto, was stirred for 16 hours at 45° C. The reaction mixture was then diluted with chloroform, washed with water and saturated brine successively, dried over sodium sulfate anhydride, and concentrated. The residue was recrystallized from hexane-ethyl acetate mixed solution, thereby yielding 1.107 g of the aimed compound as colorless crystals. According to the comparison by using TLC and 1H-NMR, this product was identified as the aimed compound obtained by Example 1-1 (2).

Provenance & Evidence