1-[2-(4-nitrophenoxy)ethyl]-1,2,4-triazole → HCID 4295342, compound

HRID 856723Notes

Reaction equation

HRID 856723 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][CH2:9][CH2:10][N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)=[CH:6][CH:5]=1)([O-])=O.[Cl-].[Ca+2].[Cl-]>C(O)C>[N:11]1([CH2:10][CH2:9][O:8][C:7]2[CH:16]=[CH:17][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH:15]=[N:14][CH:13]=[N:12]1

Participants

4

Reactant 2

HCID 8387011-[2-(4-nitrophenoxy)ethyl]-1,2,4-triazoleHCID 5284359Calcium Chloride

Product 1

HCID 4295342HCID 4295342, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(4-nitrophenoxy) ethanol (3.0 g) was dissolved in THF (60 ml), triethylamine (2.74 ml) and methanesulfonyl chloride (1.4 ml) were added to the mixture, and the mixture was stirred for 1 hour at room temperature. The reaction solution was added to water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and a solution (15 ml) of the obtained residue in DMF was added dropwise to a solution (30 ml) of 1,2,4-triazole (1.0 g) and potassium carbonate (3.4 g) in DMF. The mixture was stirred for 16 hours at 90° C., and cooled to room temperature. The reaction solution was added to water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography to give 1-[2-(4-nitrophenoxy)ethyl]-1,2,4-triazole (1.7 g). To 1-[2-(4-nitrophenoxy)ethyl]-1,2,4-triazole (1.6 g) was added 85% ethanol solution (48 ml), calcium chloride (0.38 g) and reduced iron (1.91 g) were added to the mixture, and the mixture was heated to reflux for 3 hours. After cooling to room temperature, the mixture was filtered with Celite, and washed with ethyl acetate. The solvent was removed under reduced pressure, and the obtained residue was dissolved in ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give 4-[2-(1,2,4-triazol-1-yl)ethoxy]aniline (0.92 g).

Workup

  1. additionwere added to the mixture
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 3 hours
  4. filtrationthe mixture was filtered with Celite
  5. washwashed with ethyl acetate
  6. customThe solvent was removed under reduced pressure
  7. dissolutionthe obtained residue was dissolved in ethyl acetate
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried over magnesium sulfate
  10. customThe solvent was removed under reduced pressure
  11. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d6048af13da847dd8d81004f7ef36e59
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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