Triethylamine → 5-[2-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]ethenyl]-1,3,4-oxadiazole-2(3H)-one

HRID 466049Notes

Reaction equation

HRID 466049 reaction equation
[C:1](C1NC=CN=1)(C1NC=CN=1)=[O:2].[CH3:13][C:14]([C:17]1[CH:18]=[C:19]([CH:26]=[C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])[C:28]=1[OH:29])[CH:20]=[CH:21][C:22]([NH:24][NH2:25])=[O:23])([CH3:16])[CH3:15].C(N(CC)CC)C>O1CCCC1>[CH3:31][C:30]([C:27]1[CH:26]=[C:19]([CH:20]=[CH:21][C:22]2[O:23][C:1](=[O:2])[NH:25][N:24]=2)[CH:18]=[C:17]([C:14]([CH3:13])([CH3:15])[CH3:16])[C:28]=1[OH:29])([CH3:33])[CH3:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 730977023,5-Bis(1,1-dimethylethyl)-4-hydroxycinnamic acid hydrazide

Product 1

HCID 1360412775-[2-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]ethenyl]-1,3,4-oxadiazole-2(3H)-oneYield 105.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Carbonyl diimidazole (0.7 g, 0.004 mole) is added in one portion to a stirred 0° C. solution of 3,5-bis(1,1-dimethylethyl)-4-hydroxy-cinnamic acid hydrazide (1.0 g, 0.003 mole) and triethylamine (0.4 g, 0.004 mole) in tetrahydrofuran (12 ml). The mixture is stirred at 0° C. for 15 minutes and then allowed to warm to room temperature and stir 45 minutes. The solution is concentrated and the residue dissolved in ether (50 ml) and washed with aqueous 2M HCl. The product is extracted from the organic layer by treatment with aqueous 1M NaOH (20 ml). The aqueous extract is made acidic by treatment with cold aqueous 2M HCl and the product is extracted with ether. The organic layer is washed with saturated aqueous NaCl and dried over MgSO4. Filtration and concentration provided a solid which was recrystallized from ethyl acetate/hexane to give 1.0 g (1.1 g theor., 94%) of 5-[2-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]ethenyl]-1,3,4-oxadiazole-2(3H)-one, mp >260° C.

Workup

  1. temperatureto warm to room temperature
  2. stirringstir 45 minutes
  3. concentrationThe solution is concentrated
  4. dissolutionthe residue dissolved in ether (50 ml)
  5. washwashed with aqueous 2M HCl
  6. extractionThe product is extracted from the organic layer by treatment with aqueous 1M NaOH (20 ml)
  7. extractionThe aqueous extract
  8. extractionthe product is extracted with ether
  9. washThe organic layer is washed with saturated aqueous NaCl
  10. dry with materialdried over MgSO4
  11. filtrationFiltration and concentration
  12. customprovided a solid which
  13. customwas recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-f753dac5ea5f423c9453e838761c93d7
Source dataset
uspto-grants-1992_10
Patent number
US05155122

Reaction notes

Loading…