Sulfoxonium, trimethyl-, iodide (1:1) → HCID 13080456, compound

HRID 569705Notes

Reaction equation

HRID 569705 reaction equation
[CH3:1][O-].[Na+].[I-].C[S+](C)(C)=O.[CH3:10][C:11]([C:14]([CH2:16][N:17]1[N:21]=[CH:20][N:19]=[CH:18]1)=[O:15])([CH3:13])[CH3:12]>CS(C)=O.O1CCCC1>[C:11]([C:14]1([CH2:16][N:17]2[CH:18]=[N:19][CH:20]=[N:21]2)[CH2:1][O:15]1)([CH3:10])([CH3:12])[CH3:13]

Participants

6

Reactant 3

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 1008773,3-Dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanoneHCID 10942334Sodium Methoxide

Product 1

HCID 13080456HCID 13080456, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

6 g (0.11 mol) of sodium methylate were introduced in portions into a suspension of 24 g (0.11 mol) of trimethylsulphoxonium iodide in 24 g of dimethylsulphoxide. 10 ml of tetrahydrofuran were also added, and the reaction mixture was then stirred for 5 hours at room temperature. Thereafter, a solution of 16.8 g (0.1 mol) of 1,2,4-triazol-1-yl-pinacolin in 100 ml of tetrahydrofuran was added dropwise, and the mixture was heated at 70° C. for 5 hours. The reaction mixture was filtered, and the filtrate was concentrated in vacuo. The residue was dissolved in chloroform, and the solution was washed with water, dried over sodium sulphate, filtered and concentrated. 13.8 g of a 69.4% pure 2-tert.-butyl-2-(1,2,4-triazol-1-yl-methyl)-oxirane of refractive index nD20 =1.4872 were obtained.

Workup

  1. temperaturethe mixture was heated at 70° C. for 5 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. dissolutionThe residue was dissolved in chloroform
  5. washthe solution was washed with water
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-898029fc29b94891a58952066b824bc7
Source dataset
uspto-grants-1988_03
Patent number
US04734126

Reaction notes

Loading…