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 1938752Notes

Reaction equation

HRID 1938752 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-hydroxy-tridecane 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%). (found): C, 69.25; H, 8.08; N, 7.68. ##STR13##

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-e5c64d43bf384f0e89bc17164c955232
Source dataset
uspto-grants-1997_12
Patent number
US05693657

Reaction notes

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