Triethylamine → 5-Dodecanamido-2-benzimdazolone

Participants

Reaction Steps

5-Aminobenzimidazolone (0.95 g, 6.36 mmol), triethylamine (1.1 mL, 7.89 mmol), N-methylpyrrolidinone (NMP, 5 mL), and dry THE (8 mL) are mixed in a 100 mL round bottom flask under an inert atmosphere. To this solution, a second solution of 2-decyltetradecanoyl chloride from Step I dissolved in dry THE (30 mL) is slowly added. After stirring overnight, deionized water (50 mL) is added and the THF removed by rotary evaporation to give an aqueous slurry. The solid was collected by vacuum filtration and washed with deionized water before suspending in methanol (60 mL) and heating to reflux. The suspension was then cooled and the solid was filtered and washed with fresh methanol to give 5-dodecanamido-2-benzimdazolone as a white powder (1.63 g). The product is identified by 1H and 13C NMR spectroscopy and ESI-MS and is of satisfactory purity.

Provenance & Evidence