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

HRID 1284906Notes

Reaction equation

HRID 1284906 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(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

4

Reactant 2

HCID 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 mol) of 2-(4-chlorophenoxymethyl)-2-tert.-butyloxirane and 24.15 g (0.35 mol) of 1,2,4-triazole in 120 ml of ethanol are heated under reflux for 48 hours. The mixture is then evaporated and the residue is taken up in 200 ml of ethyl acetate and heated. It is then cooled in an ice bath and the solid material is filtered off with suction and washed with ethyl acetate. The filtrate is evaporated, the residue is dissolved in ether/hexane and hydrogen chloride is passed through. The precipitate is filtered off with suction, washed with ether and the free base is obtained by addition of ethyl acetate/1 N sodium hydroxide solution. 60.2 g (65% of theory) of 2-(4-chlorophenoxymethyl)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-2-butanol of melting point 84° to 87° C. are obtained.

Workup

  1. temperatureunder reflux for 48 hours
  2. customThe mixture is then evaporated
  3. temperatureheated
  4. temperatureIt is then cooled in an ice bath
  5. filtrationthe solid material is filtered off with suction
  6. washwashed with ethyl acetate
  7. customThe filtrate is evaporated
  8. dissolutionthe residue is dissolved in ether/hexane
  9. filtrationThe precipitate is filtered off with suction
  10. washwashed with ether
  11. customthe free base is obtained by addition of ethyl acetate/1 N sodium hydroxide solution

Sources & evidence

ORD record
ord-4ccc6f91cf29400fb492a53e103dfd67
Source dataset
uspto-grants-1986_01
Patent number
US04564622

Reaction notes

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