1H-1,2,4-Triazole → 1-(4-Chlorophenyl)-3-(1,2,4-triazol-1-yl)-2-propanol

HRID 2107065

Reaction equation

HRID 2107065 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH:7]1[CH:11]=[N:10][CH:9]=[N:8]1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH:20]2[O:22][CH2:21]2)=[CH:15][CH:14]=1>C(#N)C>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:19][CH:20]([OH:22])[CH2:21][N:7]2[CH:11]=[N:10][CH:9]=[N:8]2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 148012Oxirane, 2-((4-chlorophenyl)methyl)-

Product 1

HCID 230476741-(4-Chlorophenyl)-3-(1,2,4-triazol-1-yl)-2-propanol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of potassium carbonate (8.14 g) and 1,2,4-triazole (8.14 g) in acetonitrile (100 ml) was added 1-(4-chlorophenyl)-2,3-epoxypropane (9.0 g), and the resulting suspension was heated to 70° for 4.5 h. The excess acetonitrile was evaporated under reduced pressure, and the residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with water and dried, and the solvent was evaporated to give a colourless oil. Purification by column chromatography on silica, eluting with chloroform/methanol, 95:5 by volume, gave 1-(4-chlorophenyl)-3-(1,2,4-triazol-1-yl)-2-propanol as a colourless oil which crystallised on standing, m.p. 104°-6°.

Workup

  1. temperaturethe resulting suspension was heated to 70° for 4.5 h
  2. customThe excess acetonitrile was evaporated under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. washwashed with water
  6. customdried
  7. customthe solvent was evaporated
  8. customto give a colourless oil
  9. customPurification by column chromatography on silica
  10. washeluting with chloroform/methanol, 95:5 by volume

Sources & evidence

ORD record
ord-84fc1dc50ae94feab1ac728387b645d9
Source dataset
uspto-grants-1990_06
Patent number
US04933357

Linked notes

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