1H-1,2,4-Triazole → 1,1-bis(5-chloropyrid-2-yl)-2-(1H-1,2,4-triazol-1-yl)ethanol

HRID 371181Notes

Reaction equation

HRID 371181 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][N:12]=3)[CH2:10][O:9]2)=[N:6][CH:7]=1.[NH:18]1[CH:22]=[N:21][CH:20]=[N:19]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][N:12]=2)([OH:9])[CH2:10][N:18]2[CH:22]=[N:21][CH:20]=[N:19]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 202745202,2-Bis(5-chloro-pyrid-2-yl)oxirane

Product 1

HCID 202745161,1-bis(5-chloropyrid-2-yl)-2-(1H-1,2,4-triazol-1-yl)ethanolYield 47.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

2,2-Bis(5-chloro-pyrid-2-yl)oxirane (0.8 g), 1,2,4-triazole (1.0 g) and anhydrous potassium carbonate (3.0 g) were stirred in dry N,N-dimethylformamide (30 ml) and the mixture was heated at 85° C. for 1.5 hours. The solvent was then evaporated under vacuum, with the addition of xylene to remove final traces of N,N-dimethylformamide as an azeotrope, and the residue was dissolved in water (20 ml) and extracted with ethyl acetate (3×20 ml). The combined organic extracts were dried over megnesium sulfate and evaporated. The residue was chromatographed on silica, eluting with ethyl acetate. Evaporation of the relevant fractions gave a viscous oil which solidified on trituration with petroleum ether (b.p. 60°-80° C.). Recrystallization from hexane gave the title compound as white crystals (0.48 g, 38%) m.p. 98°-100° C.

Workup

  1. customThe solvent was then evaporated under vacuum, with the addition of xylene
  2. customto remove final traces of N,N-dimethylformamide as an azeotrope
  3. dissolutionthe residue was dissolved in water (20 ml)
  4. extractionextracted with ethyl acetate (3×20 ml)
  5. dry with materialThe combined organic extracts were dried over megnesium sulfate
  6. customevaporated
  7. customThe residue was chromatographed on silica
  8. washeluting with ethyl acetate
  9. customEvaporation of the relevant fractions
  10. customgave a viscous oil which
  11. customRecrystallization from hexane

Sources & evidence

ORD record
ord-c02b2df88220435082c29a8f87cc9513
Source dataset
uspto-grants-1985_07
Patent number
US04529799

Reaction notes

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