1H-1,2,4-Triazole → 1,3-Bis(1H-1,2,4-triazol-1-yl)-2-(4-chlorophenyl)-3-methylbutan-2-ol

HRID 981540Notes

Reaction equation

HRID 981540 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([N:14]3[CH:18]=[N:17][CH:16]=[N:15]3)([CH3:13])[CH3:12])[CH2:10][O:9]2)=[CH:4][CH:3]=1.[NH:19]1[CH:23]=[N:22][CH:21]=[N:20]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N:19]1([CH2:10][C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)([OH:9])[C:11]([N:14]2[CH:18]=[N:17][CH:16]=[N:15]2)([CH3:13])[CH3:12])[CH:23]=[N:22][CH:21]=[N:20]1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 133668634-Chlorophenyl-2-[2-(1,2,4-triazol-1-yl)-prop-2-yl]-oxirane

Product 1

HCID 133668651,3-Bis(1H-1,2,4-triazol-1-yl)-2-(4-chlorophenyl)-3-methylbutan-2-olYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(4-chlorophenyl)-2-[2-(1H-1,2,4-triazol-1-yl)prop-2-yl]oxirane (1.1 g.), 1,2,4-triazole (2 g.), potassium carbonate (5 g.) and dry dimethylformamide (25 ml.) was heated at 80° under a nitrogen atmosphere for 16 hours. The reaction mixture was then cooled, filtered, washed with xylene and the filtrate was evaporated in vacuo. The residue was azeotroped with xylene (2×30 ml.) and then partitioned between methylene chloride (50 ml.) and water (50 ml.). The aqueous phase was extracted with methylene chloride (3×50 ml), and the combined organic phases were washed with water (50 ml.), and dried (MgSO4). The residue obtained after removal of the solvent was flash chromatographed on silica (150 g) using methylene chloride/methanol/saturated aqueous ammonia (93:7:1 v/v/v), for elution. The product-containing fractions on evaporation followed by crystallisation from ethyl acetate/hexane yielded 983 mg. (71% yield) of the title compound, m.p. 128°-9°.

Workup

  1. temperaturewas heated at 80° under a nitrogen atmosphere for 16 hours
  2. temperatureThe reaction mixture was then cooled
  3. filtrationfiltered
  4. washwashed with xylene
  5. customthe filtrate was evaporated in vacuo
  6. customThe residue was azeotroped with xylene (2×30 ml.)
  7. custompartitioned between methylene chloride (50 ml.) and water (50 ml.)
  8. extractionThe aqueous phase was extracted with methylene chloride (3×50 ml)
  9. washthe combined organic phases were washed with water (50 ml.)
  10. dry with materialdried (MgSO4)
  11. customThe residue obtained
  12. customafter removal of the solvent
  13. customchromatographed on silica (150 g)
  14. washfor elution
  15. customThe product-containing fractions on evaporation
  16. customfollowed by crystallisation from ethyl acetate/hexane
  17. customyielded 983 mg

Sources & evidence

ORD record
ord-f9a1def383dc461c81b04afe7c50deb6
Source dataset
uspto-grants-1991_02
Patent number
US04992454

Reaction notes

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