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

HRID 979456
Notes
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Reaction equation

HRID 979456 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].O>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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 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 (52.6 mmol) of 1,2,4-triazole are added, with stirring, to a solution of 0.11 g (47 mmol) of sodium in 30 ml of n-propanol at room temperature. The mixture is heated to reflux temperature and a solution of 15.4 g (47 mmol) of 2-(2,4-dichlorophenyl-tert.-butyl)-2-(1,2,4-triazol-1-ylmethyl)oxirane in 20 ml of n-propanol is added. The reaction mixture is heated under reflux for 15 hours, then cooled and added to water. The mixture is extracted with methylenechloride, and the organic phase is dried over sodium sulphate and evaporated. 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-ylmethyl)-1-(1,2,4-triazol-1-yl)-2-butanol of melting point 126° C. are obtained.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux temperature
  3. temperatureThe reaction mixture is heated
  4. temperatureunder reflux for 15 hours
  5. temperaturecooled
  6. extractionThe mixture is extracted with methylenechloride
  7. dry with materialthe organic phase is dried over sodium sulphate
  8. customevaporated
  9. customThe residue is purified by column chromatography (silica gel; ethyl acetate:cyclohexane=3:1)

Sources & evidence

ORD record
ord-04b8829cb35d4a3a9fc4d268b2273730
Source dataset
uspto-grants-1987_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04668660

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes