2,4-Dichlorobenzyl chloride → HCID 23335431, compound

HRID 903901Notes

Reaction equation

HRID 903901 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][CH:7]([N:18]2[CH:22]=[N:21][CH:20]=[N:19]2)[CH:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])[OH:9])=[CH:4][CH:3]=1.[H-].[Na+].[H][H].[Cl:29][C:30]1[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:31]=1[CH2:32]Cl>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]([N:18]2[CH:22]=[N:21][CH:20]=[N:19]2)[CH:8]([O:9][CH2:32][C:31]2[CH:34]=[CH:35][C:36]([Cl:38])=[CH:37][C:30]=2[Cl:29])[C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 72122,4-Dichlorobenzyl chlorideHCID 24758Sodium hydrideHCID 20574477HCID 20574477, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23335431HCID 23335431, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

19.2 g (0.05 mol) of 1-(4-chlorophenoxy)-2-(2,4-dichlorophenyl)-1-(1,2,4-triazol-1-yl)-ethan-2-ol were dissolved in 100 ml of dioxane and the solution was added dropwise to a mixture of 2 g of 80% strength sodium hydride in 100 ml of dioxane at 80° C. After the evolution of hydrogen had subsided, 10 g (0.05 mol) of 2,4-dichlorobenzyl chloride were added dropwise and the mixture was heated under reflux for 15 hours. After cooling, the solvent was distilled off in vacuo and the residue was taken up in 100 ml of water and 100 ml of methylene chloride. The organic phase was separated off, washed twice with 100 ml of water each time, dried over sodium sulphate and concentrated by distilling off the solvent in vacuo. The solid residue was recrystallized from ether. 9 g (31% of theory) of 1-(4-chlorophenoxy)-2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)-1-(1,2,4-triazol- 1-yl)-ethane of melting point 132°-135° C. were obtained.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 15 hours
  3. temperatureAfter cooling
  4. distillationthe solvent was distilled off in vacuo
  5. customThe organic phase was separated off
  6. washwashed twice with 100 ml of water each time
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated
  9. distillationby distilling off the solvent in vacuo
  10. customThe solid residue was recrystallized from ether

Sources & evidence

ORD record
ord-81e7ffa6816744df90626a6bf1890450
Source dataset
uspto-grants-1980_10
Patent number
US04229459

Reaction notes

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