1H-1,2,4-Triazole → Triadimefon

HRID 1759273Notes

Reaction equation

HRID 1759273 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].[Cl:12][C:13]1[CH:27]=[CH:26][C:16]([O:17][CH:18](Cl)[C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:15][CH:14]=1>CC(C)=O>[Cl:12][C:13]1[CH:27]=[CH:26][C:16]([O:17][CH:18]([N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)[C:19](=[O:24])[C:20]([CH3:22])([CH3:23])[CH3:21])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 926212-Butanone, 1-chloro-1-(4-chlorophenoxy)-3,3-dimethyl-

Product 1

HCID 39385TriadimefonYield 87.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

41.8 g (0.66 mole) of 1,2,4-triazole were dissolved in 300 ml of acetone. 93.4 g (0.72 mole) of anhydrous potassium carbonate were added to this solution, the suspension was heated to the boiling point and a solution of 156.5 g (0.6 mole) of 1-(4-chlorophenoxy)-1-chloro-3,3-dimethyl-butan-2-one in 150 ml of acetone was added dropwise at a rate such that the mixture boiled under reflux, without being heated. When the addition had ended, the mixture was heated under reflux for 15 hours in order to bring the reaction to completion; the resulting precipitate was then filtered off, washed with acetone and discarded. The filtrate was freed from solvent under a waterpump vacuum, the residue was taken up in 300 ml of toluene and the mixture was washed once with a solution of 10 g of 37% strength hydrochloric acid in 200 ml of water. The aqueous phase was separated off and discarded; the organic phase was washed with 500 ml of water and--after adding a further 400 ml of toluene--was stirred with a solution of 14.5 g of sodium hydroxide in 350 ml of water at room temperature for 6 hours. The organic phase was then separated off, washed with water until neutral and freed from solvent under a waterpump vacuum. 153.5 g (87% of theory) of 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one of melting point 75°-76° C. were obtained.

Workup

  1. temperaturethe suspension was heated to the boiling point
  2. temperatureunder reflux
  3. temperaturewithout being heated
  4. additionWhen the addition
  5. temperaturethe mixture was heated
  6. temperatureunder reflux for 15 hours in order
  7. customthe reaction to completion
  8. filtrationthe resulting precipitate was then filtered off
  9. washwashed with acetone
  10. washthe mixture was washed once with a solution of 10 g of 37% strength hydrochloric acid in 200 ml of water
  11. customThe aqueous phase was separated off
  12. washthe organic phase was washed with 500 ml of water
  13. addition--after adding a further 400 ml of toluene
  14. customThe organic phase was then separated off
  15. washwashed with water until neutral and freed from solvent under a waterpump vacuum

Sources & evidence

ORD record
ord-12a8d6fd4ccc48f1a36707bb00b22132
Source dataset
uspto-grants-1982_07
Patent number
US04339612

Reaction notes

Loading…