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

HRID 1493007Notes

Reaction equation

HRID 1493007 reaction equation
[N:1]#[C:2]Br.[CH3:4][C:5]([C:8]1[CH:9]=[C:10]([CH:15]=[C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:17]=1[OH:18])[C:11]([NH:13][NH2:14])=[O:12])([CH3:7])[CH3:6].C(=O)(O)[O-].[Na+].O>O1CCOCC1>[NH2:1][C:2]1[O:12][C:11]([C:10]2[CH:15]=[C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:17]([OH:18])=[C:8]([C:5]([CH3:4])([CH3:6])[CH3:7])[CH:9]=2)=[N:13][N:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 104229343,5-Di-tert-butyl-4-hydroxybenzohydrazide

Product 1

HCID 1354491304-(5-Amino-[1,3,4]oxadiazol-2-yl)-2,6-di-tert-butyl-phenolYield 62.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Cyanogen bromide (0.9 g, 0.0083 mole) is added to a solution of 3,5-bis(1,1-dimethylethyl)-4-hydroxybenzoic acid, hydrazide (2.2 g, 0.0083 mole) and sodium bicarbonate (0.7 g, 0.0083 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 give 1.5 g (2.4 g theor., 58%) of 4-(5-amino-1,3,4-oxadiazol-2-yl)-2,6-bis(1,1-dimethylethyl)-phenol after drying in vacuo at room temperature, mp 244°-245° 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-4ce1c7876ce34ae587634009a2cab3ed
Source dataset
uspto-grants-1994_12
Patent number
US05376670

Reaction notes

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