Acetic Acid → 3-[3,4-Bis(benzyloxy)-5-nitrophenyl]-5-methyl-1,2,4-oxadiazole

HRID 1920057Notes

Reaction equation

HRID 1920057 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([N+:27]([O-:29])=[O:28])[C:18]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:12]([NH2:15])=[N:13][OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:30](O)(=O)[CH3:31]>CN(C)C=O.[Cl-].[Na+].O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:12]2[N:15]=[C:30]([CH3:31])[O:14][N:13]=2)[CH:16]=[C:17]([N+:27]([O-:29])=[O:28])[C:18]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 86628080HCID 86628080, compound

Product 1

HCID 670370813-[3,4-Bis(benzyloxy)-5-nitrophenyl]-5-methyl-1,2,4-oxadiazole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred solution of 3,4-bis-benzyloxy-N′-hydroxy-5-nitro-benzamidine (1.0 g, 2.54 mmol) in dimethylformamide (5 mL) at room temperature was added 1,1-carbonyldiimidazole (0.494 g, 3.048 mmol) in one portion and the mixture was stirred at room temperature for ninety minutes. Thereupon, acetic acid (0.184 g, 3.067 mmol) was added dropwise and the mixture was allowed to stir for two hours at room temperature, then at 155° C. for three hours. The mixture was allowed to cool to room temperature, and poured onto ice-water (100 mL). Brine (10 mL) was added and the resulting precipitate was removed by filtration, washed with water and dried in air. The solid was then dissolved in dichloromethane (20 mL) and a spatula tip of activated charcoal was added. After stirring for twenty minutes, the suspension was filtered through celite and the filtrate was evaporated to leave a yellow oil that solidified on standing. After recrystallisation from dichloromethane/petroleum ether, 3-(3,4-bis-benzyloxy-5-nitrophenyl)-5-methyl-[1,2,4]oxadiazole was obtained as a pale yellow solid (0.537 g, 51%).

Workup

  1. stirringto stir for two hours at room temperature
  2. temperatureto cool to room temperature
  3. additionpoured onto ice-water (100 mL)
  4. customthe resulting precipitate was removed by filtration
  5. washwashed with water
  6. customdried in air
  7. dissolutionThe solid was then dissolved in dichloromethane (20 mL)
  8. additiona spatula tip of activated charcoal was added
  9. stirringAfter stirring for twenty minutes
  10. filtrationthe suspension was filtered through celite
  11. customthe filtrate was evaporated
  12. customto leave a yellow oil that solidified
  13. customAfter recrystallisation from dichloromethane/petroleum ether

Sources & evidence

ORD record
ord-9e1872c32a944ec393acbc9aa522d883
Source dataset
uspto-grants-2012_05
Patent number
US08168793B2

Reaction notes

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