Triethylamine → 5-Dodecanamido-2-benzimdazolone

HRID 1811363Notes

Reaction equation

HRID 1811363 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]2=[N:6][C:7](=[O:9])[N:8]=[C:4]2[CH:3]=1.C(N(CC)CC)C.[CH2:19]([CH:29](CCCCCCCCCCCC)[C:30](Cl)=[O:31])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>CN1CCCC1=O>[C:30]([NH:1][C:2]1[CH:11]=[CH:10][C:5]2=[N:6][C:7](=[O:9])[N:8]=[C:4]2[CH:3]=1)(=[O:31])[CH2:29][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 152505475-amino-2H-1,3-benzodiazol-2-oneHCID 539445462-Decyltetradecanoyl chloride

Product 1

HCID 670034905-Dodecanamido-2-benzimdazolone

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

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.

Workup

  1. additionare mixed in a 100 mL round bottom flask under an inert atmosphere
  2. customin dry THE (30 mL)
  3. additionis slowly added
  4. additiondeionized water (50 mL) is added
  5. customthe THF removed by rotary evaporation
  6. customto give an aqueous slurry
  7. filtrationThe solid was collected by vacuum filtration
  8. washwashed with deionized water
  9. temperatureheating to reflux
  10. temperatureThe suspension was then cooled
  11. filtrationthe solid was filtered
  12. washwashed with fresh methanol

Sources & evidence

ORD record
ord-dc9133a67d364a6a9b75908d6418db74
Source dataset
uspto-grants-2013_01
Patent number
US08362270B2

Reaction notes

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