Water → N-{[dimethyl-(4-fluorobenzyl)silyl]methyl}-1,2,4-triazole hydrochloride

HRID 1614554Notes

Reaction equation

HRID 1614554 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[Cl:6][CH2:7][Si:8]([CH3:18])([CH3:17])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1.O>C1(C)C(C)=CC=CC=1>[ClH:6].[CH3:7][Si:8]([CH2:18][N:1]1[CH:5]=[N:4][CH:3]=[N:2]1)([CH3:17])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 92571H-1,2,4-TriazoleHCID 15338764Chloromethyl-dimethyl(4-fluorobenzyl)silane

Product 1

HCID 19007220N-{[dimethyl-(4-fluorobenzyl)silyl]methyl}-1,2,4-triazole hydrochloride

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

After adding 10 g of 1,2,4-triazole to 10.8 g of chloromethyl-dimethyl-(4-fluorobenzyl)silane dissolved in 50 ml of xylene, the reaction mixture is refluxed for 8 hours, then 200 ml of water are added and the phases are separated. The organic phase is washed 3 times with a total of 150 ml of water, dried over anhydrous magnesium sulfate and after filtration the filtrate is evaporated to solvent-free. The pale yellow oily residue is dissolved in 70 ml of methyl propyl ketone, the solution is acidified to pH 4.5 by adding methanolic hydrogen chloride solution and then concentrated to a volume of 40 ml by distillation under atmospheric pressure. The crystals precipitated are filtered at 0° C. to give the named product in a yield of 6.56 g (46%), m.p.: 113°-114° C.

Workup

  1. temperaturethe reaction mixture is refluxed for 8 hours
  2. customthe phases are separated
  3. washThe organic phase is washed 3 times with a total of 150 ml of water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationafter filtration the filtrate
  6. customis evaporated to solvent-free
  7. dissolutionThe pale yellow oily residue is dissolved in 70 ml of methyl propyl ketone
  8. additionby adding methanolic hydrogen chloride solution
  9. concentrationconcentrated to a volume of 40 ml by distillation under atmospheric pressure
  10. customThe crystals precipitated
  11. filtrationare filtered at 0° C.
  12. customto give the named product in a yield of 6.56 g (46%), m.p.: 113°-114° C.

Sources & evidence

ORD record
ord-617a74698fd643bdad6eaf97cdf278db
Source dataset
uspto-grants-1993_03
Patent number
US05198446

Reaction notes

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