1H-1,2,4-Triazole → Tebuconazole

HRID 1165707Notes

Reaction equation

HRID 1165707 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 53.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 17.9 g (0.075 mol) of 2-(4-chlorophenyl-ethyl)-2-tert.-butyl-oxirane and 6.9 g (0.1 mol) of 1,2,4-triazole in 30 ml of ethanol was heated in a bomb tube at 150° C. for 20 hours. The reaction solution was allowed to cool and was concentrated. The residue was dissolved in ether, and the solution was washed three times with water and once with sodium chloride solution, and was dried over sodium sulphate and concentrated. The residue was subjected to chromatography over a silica gel column (eluent: dichloromethane/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 were obtained as a viscous oil.

Workup

  1. temperatureto cool
  2. concentrationwas concentrated
  3. dissolutionThe residue was dissolved in ether
  4. washthe solution was washed three times with water
  5. dry with materialonce with sodium chloride solution, and was dried over sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9827e34acfdd4accbbc739bcfceed399
Source dataset
uspto-grants-1990_03
Patent number
US04911750

Reaction notes

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