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

Participants

Reaction Steps

5-Aminobenzimidazolone (2.93 g, 19.6 mmol, obtained from TCI America, Oregon, USA) and triethylamine (4 mL, 28.7 mmol) were dissolved in 20 mL N-methylpyrrolidinone in a 250 mL round-bottom flask under inert atmosphere. To this solution, a second solution of 2-decyltetradecanoyl chloride from Step 1 dissolved in dry THF (150 mL) was slowly added. After stirring overnight, deionized water was added and the mixture was poured into 300 mL ethyl acetate and washed with three 100 mL portions of deionized water. The organic layer was then concentrated by rotary evaporation until a white slurry was obtained. The solid was 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 was identified by 1H and 13C NMR spectroscopy and ESI-MS and was of satisfactory purity. The compound was believed to be of the formula

Provenance & Evidence