1H-1,2,4-Triazole → Tebuconazole

HRID 1608250Notes

Reaction equation

HRID 1608250 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 mole) of 2-(4-chlorophenyl-ethyl)-2-tert.-butyl-oxirane and 6.9 g (0.1 mole) of 1,2,4-triazole in 30 ml of ethanol were heated at 150° C. in a bomb tube for 20 hours. The reaction mixture was allowed to cool and was concentrated. The residue was dissolved in ether and the ether solution was washed three times with water and once with sodium chloride solution, dried over sodium sulphate and concentrated. The residue was chromatographed over a silica gel column (mobile phase: 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 were obtained as a viscous oil.

Workup

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

Sources & evidence

ORD record
ord-fc436b76ba6d4b6097827723baf21ced
Source dataset
uspto-grants-1989_09
Patent number
US04870093

Reaction notes

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