1H-1,2,4-Triazole → Tebuconazole

HRID 1090675Notes

Reaction equation

HRID 1090675 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2([C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:12][O:11]2)=[CH:4][CH:3]=1.[NH:17]1[CH:21]=[N:20][CH:19]=[N:18]1>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([CH2:12][N:17]2[CH:21]=[N:20][CH:19]=[N:18]2)([OH:11])[C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 92571H-1,2,4-TriazoleHCID 946842-tert-Butyl-2-(2-(4-chlorophenyl)ethyl)oxirane

Product 1

HCID 86102TebuconazoleYield 53.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 17 9 g (0.075 mol) of 2-(4-chloro-phenylethyl)-2-tert.-butyl-oxirane and 6.9 g (0.1 mol) of 1,2,4-triazole in 30 ml of ethanol is heated at 150° C. in a bomb tube for 20 hours. The reaction solution is allowed to cool and is concentrated. The residue is dissolved in ether and the solution is washed three times with water and once with sodium chloride solution, dried over sodium sulphate and concentrated. The residue is chromatographed over a silica gel column (running agent: methylene chloride/ethyl acetate=1:1). 12.3 g (53.2% of theory) of 1-(4-chlorophenyl)-4,4-dimethyl-3-(1,2,4-triazol-1-yl-methyl)-pentan-3-ol obtained as a viscous oil, which can be recrystallized from acetonitrile (melting point 102° to 104° C.).

Workup

  1. temperatureto cool
  2. concentrationis concentrated
  3. dissolutionThe residue is dissolved in ether
  4. washthe solution is washed three times with water
  5. dry with materialonce with sodium chloride solution, dried over sodium sulphate
  6. concentrationconcentrated
  7. customThe residue is chromatographed over a silica gel column (running agent: methylene chloride/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-92e0168d622740b3928fd42d259e1c87
Source dataset
uspto-grants-1992_01
Patent number
US05082855

Reaction notes

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