Triethylamine → 5-Dodecanamido-2-benzimdazolone

HRID 1811363노트

반응식

HRID 1811363 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 670034905-Dodecanamido-2-benzimdazolone

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-dc9133a67d364a6a9b75908d6418db74
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362270B2

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