Dimethyl Sulfate → 4-Chlorophenyl-2-[2-(1,2,4-triazol-1-yl)-prop-2-yl]-oxirane

HRID 1085800Notes

Reaction equation

HRID 1085800 reaction equation
[I-].C[S+](C)C.S([O:11][CH3:12])(OC)(=O)=O.[N:13]1([C:18]([C:21]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)=O)([CH3:20])[CH3:19])[CH:17]=[N:16][CH:15]=[N:14]1>O1CCCC1>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([C:21]2([C:18]([N:13]3[CH:17]=[N:16][CH:15]=[N:14]3)([CH3:20])[CH3:19])[CH2:12][O:11]2)=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 75127Trimethylsulfonium iodideHCID 133668554-Chlorophenyl 2-(1,2,4-triazol-1-yl)-prop-2-yl ketone

Product 1

HCID 133668634-Chlorophenyl-2-[2-(1,2,4-triazol-1-yl)-prop-2-yl]-oxirane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

9.6 g (0.044 mole) of trimethylsulphonium iodide are dissolved in 9.6 g (0.118 mole) of dimethyl sulphate under a nitrogen atmosphere. 5.2 g (0.044 mole) of potassium tert.-butylate are added at room temperature and the mixture is subsequently stirred at room temperature for 6 hours. A solution of 9.9 g (0.0397 mole) of 4-chlorophenyl 2-(1,2,4-triazol-1-yl)-prop-2-yl ketone in 16 ml of tetrahydrofuran is then added dropwise at room temperature. The reaction mixture is subsequently led at room temperature for 15 hours and under reflux for 4 hours, cooled and filtered. The filtrate is concentrated in vacuo, the residue is discharged onto water and the mixture is extracted with methylene chloride. The organic phase is dried over sodium sulphate and concentrated in vacuo. 10.4 g (100% of theory) of 2-(4-chlorophenyl-2-[2-(1,2,4-triazol-1-yl)-prop-2-yl]-oxirane of refractive indes nD20 1.5388 are obtained. ##STR18##

Workup

  1. waitThe reaction mixture is subsequently led at room temperature for 15 hours
  2. temperatureunder reflux for 4 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated in vacuo
  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-782f5a63f9364bd98bf0b215b0ba5e42
Source dataset
uspto-grants-1991_04
Patent number
US05011850

Reaction notes

Loading…