Water → HCID 61766283, compound

HRID 1085803Notes

Reaction equation

HRID 1085803 reaction equation
N1C=NC=N1.[Na].ClC1C=CC([CH2:14][C:15]([C:18]2([CH:21]([N:23]3[CH:27]=[N:26][CH:25]=[N:24]3)[CH3:22])C[O:19]2)(C)C)=CC=1.O>C(O)CC>[N:23]1([CH:21]([CH3:22])[CH:18]([OH:19])[CH2:15][CH3:14])[CH:27]=[N:26][CH:25]=[N:24]1

Participants

6

Reactant 4

HCID 962WaterHCID 92571H-1,2,4-TriazoleHCID 5360545SodiumHCID 13366864HCID 13366864, compound

Product 1

HCID 61766283HCID 61766283, compound

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent2×

Procedure

3.6 g (0.052 mole) of 1,2,4-triazole are added to a solution of 0.1 g (0.043 mole) of sodium in 30 ml of n-propanol at room temperature, while stirring. A solution of 13.2 g (0.043 mole) of 2-(4-chlorophenyl-tert.-butyl)-2-[1-(1,2,4-triazol-1-yl)-ethyl]-oxirane in 20 ml of n-propanol is then added. The reaction mixture is heated under reflux for 20 hours and then cooled and poured onto 300 ml of water. The mixture is extracted with methylene chloride and the methylene chloride phase is washed with water, dried over sodium Sulphate and concentrated in vacuo. The residue is purified by column chromatography (silica gel; ethyl acetate:ether=3:1). 4 g (24.8% of theory) of 1-(4-chlorophenyl)-2,2-dimethyl-3-(1,2,4-triazol-1-yl)-methyl)-4-(1,2,4-triazol-1-yl)-3-pentanol of melting point 59° C. are obtained.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 20 hours
  3. temperaturecooled
  4. extractionThe mixture is extracted with methylene chloride
  5. washthe methylene chloride phase is washed with water
  6. dry with materialdried over sodium Sulphate
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by column chromatography (silica gel; ethyl acetate:ether=3:1)

Sources & evidence

ORD record
ord-b5565cb984fb4604a53acd82f4b36785
Source dataset
uspto-grants-1991_04
Patent number
US05011850

Reaction notes

Loading…