1H-1,2,4-Triazole → 1,3-Bis(1H-1,2,4-triazol-1-yl)-2-(4-chlorophenyl)-3-methylbutan-2-ol

HRID 1085799Notes

Reaction equation

HRID 1085799 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[Na].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2([C:17]([N:20]3[CH:24]=[N:23][CH:22]=[N:21]3)([CH3:19])[CH3:18])[CH2:16][O:15]2)=[CH:10][CH:9]=1>C(O)CC>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([OH:15])([C:17]([N:20]2[CH:24]=[N:23][CH:22]=[N:21]2)([CH3:18])[CH3:19])[CH2:16][N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 5360545SodiumHCID 133668634-Chlorophenyl-2-[2-(1,2,4-triazol-1-yl)-prop-2-yl]-oxirane

Product 1

HCID 133668651,3-Bis(1H-1,2,4-triazol-1-yl)-2-(4-chlorophenyl)-3-methylbutan-2-olYield 24.2%

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 0.11 g (0.047 mole) of sodium in 30 ml of n-propanol at room temperature, while stirring. The mixture is heated to the reflux temperature and a solution of 2-(4-chlorophenyl)-2-[2-(1,2,4-triazol-1-yl)prop-2-yl]-oxirane in 20 ml of n-propanol is added. The reaction mixture is heated under reflux for 15 hours and then cooled and poured onto water. The mixture is extracted with methylene chloride and the organic phase is dried over sodium sulphate and concentrated. The residue is purified by column chromatography (silica gel; chloroform:methanol=9:1). 3.7 g (24.2% of theory) of 2-(4-chlorophenyl)-1,3-di-(1,2,4-triazol-1-yl)-3-methyl-2-butanol of melting point 114° C. are obtained.

Workup

  1. temperatureThe mixture is heated to the reflux temperature
  2. temperatureThe reaction mixture is heated
  3. temperatureunder reflux for 15 hours
  4. temperaturecooled
  5. additionpoured onto water
  6. extractionThe mixture is extracted with methylene chloride
  7. dry with materialthe organic phase is dried over sodium sulphate
  8. concentrationconcentrated
  9. customThe residue is purified by column chromatography (silica gel; chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-8eb319d7b0cc4f8dba883b0698216725
Source dataset
uspto-grants-1991_04
Patent number
US05011850

Reaction notes

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