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

HRID 1811362Notes

Reaction equation

HRID 1811362 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) 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.

Workup

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

Sources & evidence

ORD record
ord-176370027fcc4135bf3db3f8605e61d6
Source dataset
uspto-grants-2013_01
Patent number
US08362270B2

Reaction notes

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