Bis-(1H-imidazol-2-YL)-methanone → 2-(3-Dodecyl-[1,2,4]oxadiazol-5-yl)-2-phenyl-N-(2,4,6-trimethoxy-phenyl)-acetamide

HRID 1756991Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1756991
C(C1NC=CN=1)(C1NC=CN=1)=O.[CH3:13][O:14][C:15]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23][CH3:24])[C:16]=1[NH:25][C:26]([CH:28]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:29](O)=[O:30])=[O:27].O[NH:39][C:40](=[NH:53])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52]>C1COCC1>[CH2:41]([C:40]1[N:39]=[C:29]([CH:28]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:26]([NH:25][C:16]2[C:17]([O:23][CH3:24])=[CH:18][C:19]([O:21][CH3:22])=[CH:20][C:15]=2[O:14][CH3:13])=[O:27])[O:30][N:53]=1)[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52]

Komponenten

5

Edukt 3

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 10665192alpha-[[(2,4,6-Trimethoxyphenyl)amino]carbonyl]benzene acetic acidHCID 178443206HCID 178443206, Verbindung

Produkt 1

HCID 107211272-(3-Dodecyl-[1,2,4]oxadiazol-5-yl)-2-phenyl-N-(2,4,6-trimethoxy-phenyl)-acetamideAusbeute 11 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Carbonyl dimidazole (0.28 g, 1.71 mmol) was added to a solution of α-[[(2,4,6-trimethoxyphenyl)amino]carbonyl]-benzene acetic acid (0.56 g, 1.63 mmol) in dry THF (20 mL), and the resulting mixture was stirred at room temperature for 1 hour, then N-hydroxytridecane imidamide (0.37 g, 1.63 mmol) was added, and the mixture stirred for 1.5 hours, concentrated in vacuo, dissolved in glacial acetic acid, and refluxed for 1.5 hours. The solution was concentrated and azeotroped with benzene (2×25 mL), dissolved in ethyl acetate, and washed with NaHCO3, water, brine, dried with MgSO4, and recrystallized from ethanol/water to yield a white solid (0.093 g, 11%).

Aufarbeitung

  1. stirringthe mixture stirred for 1.5 hours
  2. concentrationconcentrated in vacuo
  3. dissolutiondissolved in glacial acetic acid
  4. temperaturerefluxed for 1.5 hours
  5. concentrationThe solution was concentrated
  6. customazeotroped with benzene (2×25 mL)
  7. dissolutiondissolved in ethyl acetate
  8. washwashed with NaHCO3, water, brine
  9. dry with materialdried with MgSO4
  10. customrecrystallized from ethanol/water

Quellen und Nachweise

ORD-Eintrag
ord-3819cd485a7a4d70a5848790e063d516
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05441975

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