Triethylamine → 5-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3,4-oxadiazol-2(3H)-one

HRID 1657061Notes

Reaction equation

HRID 1657061 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[CH3:13][C:14]([C:17]1[CH:18]=[C:19]([CH:24]=[C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:26]=1[OH:27])[C:20]([NH:22][NH2:23])=[O:21])([CH3:16])[CH3:15].C(N(CC)CC)C>O1CCCC1>[CH3:16][C:14]([C:17]1[CH:18]=[C:19]([C:20]2[O:21][C:1](=[O:2])[NH:23][N:22]=2)[CH:24]=[C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:26]=1[OH:27])([CH3:13])[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 104229343,5-Di-tert-butyl-4-hydroxybenzohydrazide

Product 1

HCID 1355035925-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3,4-oxadiazol-2(3H)-oneYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1'-Carbonyl dimidazole (0.8 g, 0.005 mole) is added in one portion to a stirred 0° C. solution of 3,5-bis(1,1-dimethylethyl)-4-hydrox-ybenzoic acid hydrazide (1.0 g, 0.004 mole) and triethylamine (0.6 ml, 0.004 mole) in tetrahydrofuran (12 ml). After 18 hours the mixture is concentrated in vacuo and the residue dissolved in ether. The solution is washed with aqueous 2M HCl, saturated aqueous NaHCO3, saturated aqueous NaCl, and dried over MgSO4. Filtered and concentrated in vacuo to obtain a residue which is purified by flash chromatography using 10% ethyl acetate/hexane eluent. Recrystallize from ethyl acetate/hexane to obtain 0.6 g (1.1 g theor., 55%) 5-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-1,3,4-oxadiazol-2(3H)-one, mp 246° C.

Workup

  1. concentrationAfter 18 hours the mixture is concentrated in vacuo
  2. dissolutionthe residue dissolved in ether
  3. washThe solution is washed with aqueous 2M HCl, saturated aqueous NaHCO3, saturated aqueous NaCl
  4. dry with materialdried over MgSO4
  5. filtrationFiltered
  6. concentrationconcentrated in vacuo
  7. customto obtain a residue which
  8. customis purified by flash chromatography
  9. customRecrystallize from ethyl acetate/hexane

Sources & evidence

ORD record
ord-a6efba1e3908403799d6f57f40313365
Source dataset
uspto-grants-1993_10
Patent number
US05256680

Reaction notes

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