Ethyl Acetate → alpha-((4-Chlorophenoxy)methyl)-alpha-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol

HRID 330439Notes

Reaction equation

HRID 330439 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][C:8]2([C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:10][O:9]2)=[CH:4][CH:3]=1.[NH:17]1[CH:21]=[N:20][CH:19]=[N:18]1.C(OCC)(=O)C>C(O)C>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][C:8]([OH:9])([C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:10][N:17]2[CH:21]=[N:20][CH:19]=[N:18]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 92571H-1,2,4-TriazoleHCID 127636212-tert-Butyl-2-[(4-chlorophenoxy)methyl]oxirane

Product 1

HCID 123676alpha-((4-Chlorophenoxy)methyl)-alpha-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanolYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

72.15 g (0.3 mole) of 2-(4-chlorophenoxy-methyl)-2-tert.-butyl-oxirane and 24.15 g (0.35 mole) of 1,2,4-triazole were heated under reflux in 120 ml of ethanol for 48 hours. The mixture was then concentrated, the residue was taken up in 200 ml of ethyl acetate and the ethyl acetate mixture was heated. It was then cooled in an ice bath and the solid was filtered off and rinsed with ethyl acetate. The filtrate was concentrated, the residue was dissolved in ether/hexane and the solution was gassed with hydrogen chloride. The precipitate was filtered off and rinsed with ether and the free base was obtained by adding ethyl acetate/1N sodium hydroxide solution. 60.2 g (65% of theory) of 2-(4-chlorophenoxy-methyl)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-ol of melting point 84°-87° C. were obtained.

Workup

  1. concentrationThe mixture was then concentrated
  2. temperaturethe ethyl acetate mixture was heated
  3. temperatureIt was then cooled in an ice bath
  4. filtrationthe solid was filtered off
  5. washrinsed with ethyl acetate
  6. concentrationThe filtrate was concentrated
  7. dissolutionthe residue was dissolved in ether/hexane
  8. filtrationThe precipitate was filtered off
  9. washrinsed with ether
  10. customthe free base was obtained

Sources & evidence

ORD record
ord-37d0373e89ea449f84c8f278c252e002
Source dataset
uspto-grants-1990_01
Patent number
US04897107

Reaction notes

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