Water → 5-(2'-Decyltetradecanamido)-2-benzimidazolone

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Reaction Steps

5-Aminobenzimidazolone (2.93 g, 19.6 mmol) and triethylamine (4 mL, 28.7 mmol) are dissolved in 20 mL of N-methylpyrrolidinone (NMP) in a 250 mL round bottom flask under an inert atmosphere. To this solution, a second solution of 2-decyltetradecanoyl chloride from Step I dissolved in dry THF (150 mL) is slowly added. After stirring overnight, deionized water is added and the mixture is poured in to 300 mL of ethyl acetate and washed with three 100 mL portions of deionized water. The organic layer is then concentrated by rotary evaporation until a white slurry is obtained. The solid is collected by filtration and washed with cold ethyl acetate to give 5-(2′-decyltetradecanamido)-2-benzimidazolone as a white solid (7.18 g). The product is identified by 1H and 13C NMR spectroscopy and ESI-MS and is of satisfactory purity.

Provenance & Evidence