1H-1,2,4-Triazole → 4-(2,4-Dichlorophenyl)-3,3-dimethyl-2-(1,2,4-triazol-1-ylmethyl)-1-(1,2,4-triazol-1-yl)-2-butanol

HRID 329944Notes

Reaction equation

HRID 329944 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[Na].[Cl:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[CH2:15][C:16]([C:19]1([CH2:22][N:23]2[CH:27]=[N:26][CH:25]=[N:24]2)[CH2:21][O:20]1)([CH3:18])[CH3:17]>C(O)CC>[Cl:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[CH2:15][C:16]([CH3:18])([CH3:17])[C:19]([CH2:22][N:23]1[CH:27]=[N:26][CH:25]=[N:24]1)([OH:20])[CH2:21][N:1]1[CH:5]=[N:4][CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 5360545SodiumHCID 133403832-(2,4-Dichlorophenyl-tert.-butyl)-2-(1,2,4-triazol-1-ylmethyl)oxirane

Product 1

HCID 133403844-(2,4-Dichlorophenyl)-3,3-dimethyl-2-(1,2,4-triazol-1-ylmethyl)-1-(1,2,4-triazol-1-yl)-2-butanolYield 18.8%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent2×

Procedure

3.7 g (52.5 millimoles) of 1,2,4-triazole are added to a solution of 0.11 g (47 millimoles) 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 15.4 g (47 millimoles) of 2-(2,4-dichlorophenyl-tert.-butyl)-2-(1,2,4-triazol-1-yl-methyl)-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; ethyl acetate:cyclohexane=3:1). 3.5 g (18.8% of theory) of 4-(2,4-dichlorophenyl)-3,3-dimethyl-2-(1,2,4-triazol-1-yl-methyl)-1-(1,2,4-triazol-1-yl)-2-butanol of melting point 126° 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; ethyl acetate:cyclohexane=3:1)

Sources & evidence

ORD record
ord-6d9d7e821eed4fc9b63064670a124af7
Source dataset
uspto-grants-1990_01
Patent number
US04894382

Reaction notes

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