Sodium hydride → 1H-1,2,4-Triazole, 1-[[2-(2,4-dichlorophenyl)oxiranyl]methyl]-

HRID 1979714Notes

Reaction equation

HRID 1979714 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[N:9]1([CH2:14][C:15]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])=[O:16])[CH:13]=[N:12][CH:11]=[N:10]1>C(OCC)C.CS(C)=O>[Cl:24][C:18]1[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:17]=1[C:15]1([CH2:14][N:9]2[CH:13]=[N:12][CH:11]=[N:10]2)[CH2:4][O:16]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 7393741-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone

Product 1

HCID 104232291H-1,2,4-Triazole, 1-[[2-(2,4-dichlorophenyl)oxiranyl]methyl]-Yield 34.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

Sodium hydride (3.78 g, 0.079 mole as 50% dispersion in oil) was suspended, with stirring, in 20 ml of dry diethyl ether. The ether was then removed by decantation, and the sodium hydride was dried in a stream of dry nitrogen. 100 ml of dry dimethylsulphoxide was added followed by 17.34 (0.079 mole) of dry powdered trimethylsulphoxonium iodide, in portions, over 15 minutes. The resulting mixture was stirred for 30 minutes at room temperature (20° C.). 2-(1H-1,2,4-Triazol-1-yl)-2',4'-dichloro acetophenone (18.33 g, 0.072 mole) as a solution in 50 ml of dry dimethylsulphoxide was then added. The mixture was heated at 60° C. for 3 hours and allowed to stand at room temperature overnight. The reaction mixture was cooled and quenched in ice. The product was then extracted into ethyl acetate (600 ml). The ethyl acetate layer was separated, dried over magnesium sulphate, and concentrated to give a red gum. Column chromatography of the gum on silica, eluting with ether, gave 6.62 g (34.4%) of the title compound as a gum.

Workup

  1. customThe ether was then removed by decantation
  2. dry with materialthe sodium hydride was dried in a stream of dry nitrogen
  3. addition100 ml of dry dimethylsulphoxide was added
  4. temperatureThe mixture was heated at 60° C. for 3 hours
  5. waitto stand at room temperature overnight
  6. temperatureThe reaction mixture was cooled
  7. customquenched in ice
  8. extractionThe product was then extracted into ethyl acetate (600 ml)
  9. customThe ethyl acetate layer was separated
  10. dry with materialdried over magnesium sulphate
  11. concentrationconcentrated
  12. customto give a red gum
  13. washColumn chromatography of the gum on silica, eluting with ether

Sources & evidence

ORD record
ord-c56c8393bd57401fa4ad19dd6947741c
Source dataset
uspto-grants-1984_11
Patent number
US04482558

Reaction notes

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