Dimethyl Sulfoxide → 1-{2-[(2-chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-1,2,4-triazole

HRID 745285Notes

Reaction equation

HRID 745285 reaction equation
[N+]([O:4][CH:5]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[Cl:19])[CH2:6][N:7]1[CH:11]=[N:10][CH:9]=[N:8]1)([O-])=O.[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27]Cl.[H-].[Na+].CS(C)=O>O.C1C=CC=CC=1>[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][O:4][CH:5]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[Cl:19])[CH2:6][N:7]1[CH:11]=[N:10][CH:9]=[N:8]1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 119062-Chlorobenzyl chlorideHCID 24758Sodium hydrideHCID 54558181alpha-(2,4-dichlorophenyl)-1H-1,2,4-triazole-1-ethanol nitrate

Product 1

HCID 136554311-{2-[(2-chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-1,2,4-triazole

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

A mixture of 3.2 parts of α-(2,4-dichlorophenyl)-1H-1,2,4-triazole-1-ethanol nitrate, 2.4 parts of 1-chloro-2-(chloromethyl)benzene, 1.5 parts of a sodium hydride dispersion 50%, 70 parts of dimethyl sulfoxide and 63 parts of benzene is stirred for 2.50 hours at room temperature. Water is added and the product is extracted twice with 2,2'-oxybispropane. The extract is washed twice with water and the solvent is removed in vacuo. The residue is crystallized from 2,2'-oxybispropane, yielding 3 parts of 1-{2-[(2-chlorophenyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}-1H-1,2,4-triazole; mp. 106.4° C.

Workup

  1. extractionthe product is extracted twice with 2,2'-oxybispropane
  2. washThe extract is washed twice with water
  3. customthe solvent is removed in vacuo
  4. customThe residue is crystallized from 2,2'-oxybispropane

Sources & evidence

ORD record
ord-2ef60ca45db148cf812a88ee38b52ade
Source dataset
uspto-grants-1986_07
Patent number
US04598085

Reaction notes

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