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

HRID 1473728Notes

Reaction equation

HRID 1473728 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]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[C:30](Cl)=[O:31])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].O>CN1CCCC1=O.C1COCC1.C(OCC)(=O)C>[CH2:19]([CH:29]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[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])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 152505475-amino-2H-1,3-benzodiazol-2-oneHCID 539445462-Decyltetradecanoyl chloride

Product 1

HCID 670044425-(2'-Decyltetradecanamido)-2-benzimidazolone

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

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

Workup

  1. additionwas slowly added
  2. additionwas added
  3. washwashed with three 100 mL portions of deionized water
  4. concentrationThe organic layer was then concentrated by rotary evaporation until a white slurry
  5. customwas obtained
  6. filtrationThe solid was collected by filtration
  7. washwashed with cold ethyl acetate

Sources & evidence

ORD record
ord-41bd261ddabc47f5b41e064356ab7517
Source dataset
uspto-grants-2015_04
Patent number
US09017701B2

Reaction notes

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