1H-1,2,4-Triazole → 1,4-Bis-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one

HRID 1995920Notes

Reaction equation

HRID 1995920 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][CH:7](Br)[C:8](=[O:21])[C:9]([CH3:20])([CH3:19])[CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[NH:25]1[CH:29]=[N:28][CH:27]=[N:26]1.O.O.O.O.C1(S(O)(=O)=O)C2C=CC=C(S(O)(=O)=O)C=2C=CC=1>C(#N)C.CC(C)=O>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][CH:7]([N:25]2[CH:29]=[N:28][CH:27]=[N:26]2)[C:8](=[O:21])[C:9]([CH3:20])([CH3:19])[CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 127659701,4-Bis-(4-chlorophenoxy)-1-bromo-3,3-dimethyl-butan-2-oneHCID 53249422Naphthalene-1,5-disulfonic acid tetrahydrate

Product 1

HCID 127659711,4-Bis-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-oneYield 58.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6342AcetonitrileSolvent

Procedure

21.6 g (0.05 mol) of crude 1,4-bis-(4-chlorophenoxy)-1-bromo-3,3-dimethyl-butan-2-one were stirred under reflux with 14 g (0.2 mol) of 1,2,4-triazole in 100 ml of acetonitrile for 17 hours. The mixture was then concentrated by distilling off the solvent under reduced pressure. The residue was taken up in 400 ml of methylene chloride and the mixture was extracted by shaking three times with 800 ml of water each time, dried over sodium sulphate and concentrated. The residue was taken up in 100 ml of acetone, and 9 g (0.05 mol) of 1,5-naphthalenedisulphonic acid tetrahydrate in 50 ml of acetone were added dropwise. The precipitate formed was filtered off and suspended in 200 ml of methylene chloride. 400 ml of saturated sodium bicarbonate solution were added, the mixture was stirred for 30 minutes and the organic phase was separated off, dried over sodium sulphate and concentrated by distilling off the solvent. 12.3 g (58.6% of theory) of 1,4-bis-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one were obtained as an oil.

Workup

  1. concentrationThe mixture was then concentrated
  2. distillationby distilling off the solvent under reduced pressure
  3. extractionthe mixture was extracted
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. customThe precipitate formed
  7. filtrationwas filtered off
  8. addition400 ml of saturated sodium bicarbonate solution were added
  9. stirringthe mixture was stirred for 30 minutes
  10. customthe organic phase was separated off
  11. dry with materialdried over sodium sulphate
  12. concentrationconcentrated
  13. distillationby distilling off the solvent

Sources & evidence

ORD record
ord-890004aa001147fe8f59d58af7813962
Source dataset
uspto-grants-1983_09
Patent number
US04406909

Reaction notes

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