Sulfoxonium, trimethyl-, iodide (1:1) → 2-(2,4-Dichlorophenyl-tert.-butyl)-2-(1,2,4-triazol-1-ylmethyl)oxirane

HRID 329945

Reaction equation

HRID 329945 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[Cl:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[CH2:15][C:16]([CH3:26])([CH3:25])[C:17](=[O:24])[CH2:18][N:19]1[CH:23]=[N:22][CH:21]=[N:20]1>CS(C)=O.O1CCCC1>[Cl:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[CH2:15][C:16]([C:17]1([CH2:18][N:19]2[CH:23]=[N:22][CH:21]=[N:20]2)[CH2:2][O:24]1)([CH3:26])[CH3:25]

Participants

5

Reactant 2

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 133403824-(2,4-Dichlorophenyl)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butanone

Product 1

HCID 133403832-(2,4-Dichlorophenyl-tert.-butyl)-2-(1,2,4-triazol-1-ylmethyl)oxiraneYield 73.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

15.7 g (71.2 millimoles) of trimethylsulphoxonium iodide are dissolved in 16 g of dimethylsulphoxide under a nitrogen atmosphere. 9.4 g (71.2 millimoles) of potassium tert.-butylate are added at room temperature, while cooling. The mixture is subsequently stirred for 6 hours and a solution of 20 g (64.1 millimoles) of 4-(2,4-dichlorophenyl)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-2-butanone in 30 ml of tetrahydrofuran is then added. The reaction mixture is stirred at room temperature for 15 hours and under reflux for 4 hours, cooled and poured onto water. The mixture is extracted with methylene chloride and the organic phase is dried over sodium sulphate and concentrated in vacuo. 15.4 g (73.7% of theory) of 2-(2,4-dichlorophenyl-tert.-butyl)-2-(1,2,4-triazol-1-yl-methyl)-oxirane of refractive index nD20 1.5539 are obtained. ##STR13##

Workup

  1. temperaturewhile cooling
  2. stirringThe reaction mixture is stirred at room temperature for 15 hours
  3. temperatureunder reflux for 4 hours
  4. temperaturecooled
  5. additionpoured onto water
  6. extractionThe mixture is extracted with methylene chloride
  7. dry with materialthe organic phase is dried over sodium sulphate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e2278289ddc9481da80d2ae7405298b7
Source dataset
uspto-grants-1990_01
Patent number
US04894382

Linked notes

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