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

HRID 466044Notes

Reaction equation

HRID 466044 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 diimidazole (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-hydroxybenzoic 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 HC, 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 HC, 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-0824ec0fa10343ca87bec1a135fffe03
Source dataset
uspto-grants-1992_10
Patent number
US05155122

Reaction notes

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