4-Aminophenol → 4-(4H-1,2,4-Triazol-4-yl)phenol

HRID 1798812Notes

Reaction equation

HRID 1798812 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH:9]([NH:11][NH:12][CH:13]=O)=O.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.CN(C=O)C>[N:11]1[N:12]=[CH:13][N:1]([C:2]2[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=2)[CH:9]=1

Participants

6

Reactant 3

HCID 4034-AminophenolHCID 6101p-Toluenesulfonic acidHCID 123421,2-Hydrazinedicarboxaldehyde

Product 1

HCID 252395024-(4H-1,2,4-Triazol-4-yl)phenol

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

4-aminophenol (1 g, 9.16 mmol) and bisformyl hydrazine (888 mg, 10.08 mmol) were dissolved in a mixture of toluene (30 mL) and DMF (3 mL), followed by addition of pTSA (1.92 g, 10.08 mmol). The mixture was heated under reflux for 3 hours. Upon cooling, the mixture separated to two layers. The upper toluene layer was discarded. The lower dark DMF layer was directly purified by column chromatography using a 115 gram biotage silica gel cartridge eluting with 20-40 ethyl acetate/hexanes (gradient) to give the product as pale yellow solid. LRMS tale: 161.1; obs: 162.4 (M+1).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. temperatureUpon cooling
  4. customthe mixture separated to two layers
  5. customThe lower dark DMF layer was directly purified by column chromatography
  6. washeluting with 20-40 ethyl acetate/hexanes (gradient)

Sources & evidence

ORD record
ord-025192b321704f9da9a5321da0309799
Source dataset
uspto-grants-2013_01
Patent number
US08343990B2

Reaction notes

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