1H-1,2,4-Triazole → HCID 23349971, compound

HRID 2058198Notes

Reaction equation

HRID 2058198 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[NH:9]1[CH:13]=[N:12][CH:11]=[N:10]1.Br[CH:15](Br)[C:16](=[O:22])[C:17]([O:20][CH3:21])([CH3:19])[CH3:18].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:15]([N:9]2[CH:13]=[N:12][CH:11]=[N:10]2)[C:16](=[O:22])[C:17]([O:20][CH3:21])([CH3:19])[CH3:18])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 23349978HCID 23349978, compound

Product 1

HCID 23349971HCID 23349971, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 9.9 g (0.045 mole) of 4-iodophenol, 3.45 g (0.05 mole) of 1H-1,2,4-triazole, 12.33 g (0.045 mole) of 1,1-dibromo-3-methoxy-3-methyl-2-butanone, and 14 g (0.101 mole) of potassium carbonate in 200 ml of acetone was heated at boiling temperature (reflux) with stirring for 4 hours. After evaporating the solvent, 400 ml of 5% NaOH solution was added and the mixture extracted with diethyl ether. The ether phase was dried using MgSO4 and the solvent evaporated. The residual yellow oil was purified by high pressure liquid chromatography (silica gel, 8:2 hexane/acetone). Recrystallization from hexane-ether gave 8.0 g (44% yield) of 1-(4-iodophenoxy)-1-(1H-1,2,4-triazol-1-yl)-3-methoxy-3-methyl-2-butanone, m.p. 81.5°-82.5° C.

Workup

  1. temperaturewas heated at boiling temperature (reflux)
  2. customAfter evaporating the solvent, 400 ml of 5% NaOH solution
  3. additionwas added
  4. extractionthe mixture extracted with diethyl ether
  5. dry with materialThe ether phase was dried
  6. customthe solvent evaporated
  7. customThe residual yellow oil was purified by high pressure liquid chromatography (silica gel, 8:2 hexane/acetone)
  8. customRecrystallization from hexane-ether

Sources & evidence

ORD record
ord-5c80115726f0412c91099171eeacb347
Source dataset
uspto-grants-1980_07
Patent number
US04215127

Reaction notes

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