1H-1,2,4-Triazole → HCID 13259987, compound

HRID 483119Notes

Reaction equation

HRID 483119 reaction equation
[Na].[NH:2]1[CH:6]=[N:5][CH:4]=[N:3]1.[Cl:7][C:8]1[CH:9]=[C:10]([C:15]2([CH2:18][C:19]#[CH:20])[CH2:17][O:16]2)[CH:11]=[CH:12][C:13]=1[Cl:14]>C(O)CCC>[Cl:7][C:8]1[CH:9]=[C:10]([C:15]([OH:16])([CH2:17][N:2]2[CH:6]=[N:5][CH:4]=[N:3]2)[CH2:18][C:19]#[CH:20])[CH:11]=[CH:12][C:13]=1[Cl:14]

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 5360545SodiumHCID 132599842-(3,4-Dichlorophenyl)-2-(prop-2-yn-1-yl)oxirane

Product 1

HCID 13259987HCID 13259987, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

0.275 g (0.011 mol) of sodium is introduced into a boiling solution of 8.05 g (0.116 mol) of 1,2,4-triazole in 400 ml of n-butanol. 24 g (0.105 mol) of 2-(3,4-dichlorophenyl)-2-propargyl-oxirane, dissolved in 50 ml of n-butanol, are then added. The solution is heated at the boil for 12 hours, the solvent is distilled off in vacuo, the residue is taken up in 200 ml of trichloromethane, the solution is washed with twice 50 ml of water, and the organic phase is dried over anhydrous sodium sulphate and then filtered over 200 g of silica gel. 18.45 g (53.6% of theory) of 4-(3,4-dichlorophenyl)-5-(1,2,4-triazol-1-yl)-pent-1-in-4-ol are obtained as colorless crystals of melting point 114° C.

Workup

  1. additionare then added
  2. temperatureThe solution is heated at the boil for 12 hours
  3. distillationthe solvent is distilled off in vacuo
  4. washthe solution is washed with twice 50 ml of water
  5. dry with materialthe organic phase is dried over anhydrous sodium sulphate
  6. filtrationfiltered over 200 g of silica gel

Sources & evidence

ORD record
ord-7aa7bd47163c44d987bdeb3637e38c16
Source dataset
uspto-grants-1986_03
Patent number
US04578396

Reaction notes

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