1H-1,2,4-Triazole → 1-(4-Chlorophenyl)-1-[1-(3-chloro-1,2,4-triazol-1-yl)-cyclopropyl]-2-(1,2,4-triazol-1-yl)-ethan-1-ol

HRID 2371910Notes

Reaction equation

HRID 2371910 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]3([N:14]4[CH:18]=[N:17][C:16]([Cl:19])=[N:15]4)[CH2:13][CH2:12]3)[CH2:10][O:9]2)=[CH:4][CH:3]=1.[NH:20]1[CH:24]=[N:23][CH:22]=[N:21]1>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2([N:14]3[CH:18]=[N:17][C:16]([Cl:19])=[N:15]3)[CH2:13][CH2:12]2)([OH:9])[CH2:10][N:20]2[CH:24]=[N:23][CH:22]=[N:21]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 92571H-1,2,4-TriazoleHCID 146972292-(4-Chlorophenyl)-2-[1-(3-chloro-1,2,4-triazol-1-yl)-cyclopropyl]oxirane

Product 1

HCID 146972301-(4-Chlorophenyl)-1-[1-(3-chloro-1,2,4-triazol-1-yl)-cyclopropyl]-2-(1,2,4-triazol-1-yl)-ethan-1-olYield 44.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
100 °C

Procedure

A solution of 21 g (0.071 mol) of 2-(4-chlorophenyl)-2-[1-(3-chloro-1,2,4-triazol-1-yl)-cyclopropyl]-oxirane in 30 ml of absolute dimethylformamide is added dropwise at 80° C. to a stirred mixture of 15.6 g (0.276 mol) of 1,2,4-triazole and 1.7 g (0.015 mol) of potassium tert.-butylate in 40 ml of absolute dimethylformamide. The reaction mixture is stirred for 6 more hours at 100° C. and then concentrated by stripping off the solvent under reduced pressure. The residue which remains is taken up in a mixture of ethyl acetate/toluene, and the mixture is washed with water, dried over sodium sulphate and concentrated under reduced pressure. The residue is chromatographed on silica gel using a mixture of dichloromethane/ethanol=98:2 as the eluent. Concentration of the eluate by evaporation gives 11.5 g of 1-(4-chlorophenyl)-1-[1-(3-chloro-1,2,4-triazol-1-yl)-cyclopropyl]-2-(1,2,4-triazol-1-yl)-ethan-1-ol in the form of a solid of melting point 156° C.

Workup

  1. concentrationconcentrated
  2. additionThe residue which remains is taken up in a mixture of ethyl acetate/toluene
  3. washthe mixture is washed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is chromatographed on silica gel using
  7. additiona mixture of dichloromethane/ethanol=98:2 as the eluent
  8. customConcentration of the eluate by evaporation

Sources & evidence

ORD record
ord-a76cf5370b0c44878f4664493aeafc5d
Source dataset
uspto-grants-1992_03
Patent number
US05096913

Reaction notes

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