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 2380541Notes

Reaction equation

HRID 2380541 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-fc6f1a3df94a416a8cee087682d4fe4b
Source dataset
uspto-grants-1994_11
Patent number
US05366987

Reaction notes

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