Water → 4-[2-(5-Amino-[1,3,4]oxadiazol-2-yl)-vinyl]-2,6-di-tert-butyl-phenol

HRID 466060Notes

Reaction equation

HRID 466060 reaction equation
[N:1]#[C:2]Br.[CH3:4][C:5]([C:8]1[CH:9]=[C:10]([CH:17]=[C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:19]=1[OH:20])[CH:11]=[CH:12][C:13]([NH:15][NH2:16])=[O:14])([CH3:7])[CH3:6].C(=O)(O)[O-].[Na+].O>O1CCOCC1>[NH2:1][C:2]1[O:14][C:13](/[CH:12]=[CH:11]/[C:10]2[CH:9]=[C:8]([C:5]([CH3:4])([CH3:6])[CH3:7])[C:19]([OH:20])=[C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:17]=2)=[N:15][N:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 730977023,5-Bis(1,1-dimethylethyl)-4-hydroxycinnamic acid hydrazide

Product 1

HCID 1354999474-[2-(5-Amino-[1,3,4]oxadiazol-2-yl)-vinyl]-2,6-di-tert-butyl-phenolYield 52.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Cyanogen bromide (0.7 g, 0.0067 mole) is added to a solution of 3,5-bis(1,1-dimethylethyl)-4-hydroxycinnamic acid, hydrazide (1.9 g, 0.0067 mole) and sodium bicarbonate (0.56 g, 0.0067 mole) in dioxane (10 ml)/water (10 ml). The resulting mixture is stirred two hours at room temperature. The solution is concentrated to half volume in vacuo and the residue diluted with water. The resulting solid is filtered and recrystallized from ethyl acetate/hexane to provide 1.1 g (2.1 g theor., 52%) of (E)-4-[2-(5-amino-1,3,4-oxadiazole-2-yl)ethenyl]-2,6-bis(1,1-dimethylethyl)phenol after drying in vacuo at room temperature, mp 221° C.

Workup

  1. concentrationThe solution is concentrated to half volume in vacuo
  2. additionthe residue diluted with water
  3. filtrationThe resulting solid is filtered
  4. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-810b89130010468db5381a722fd223be
Source dataset
uspto-grants-1992_10
Patent number
US05155122

Reaction notes

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