1H-1,2,4-Triazole → 1-((6-Chloropyridin-2-yl)oxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one

HRID 434380Notes

Reaction equation

HRID 434380 reaction equation
ClC(Cl)C(=O)C(C)(C)C.[Cl:10][C:11]1[N:16]=[C:15]([OH:17])[CH:14]=[CH:13][CH:12]=1.N1C=NC=N1.C(=O)([O-])[O-].[K+].[K+].[N:29]1([CH:34](N2C=NC=N2)[C:35](=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37])[CH:33]=[N:32][CH:31]=[N:30]1.ClC1N=C(OC(OC2C=CC=C(Cl)N=2)C(=O)C(C)(C)C)C=CC=1>CC(C)=O>[Cl:10][C:11]1[N:16]=[C:15]([O:17][CH:34]([N:29]2[CH:33]=[N:32][CH:31]=[N:30]2)[C:35](=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37])[CH:14]=[CH:13][CH:12]=1

Participants

8

Reactant 6

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 314321,1-Dichloro-3,3-dimethyl-2-butanoneHCID 137063971,1-Bis-(1,2,4-triazol-1-yl)-3,3-dimethylbutan-2-oneHCID 204937601,1-Bis-(6-chloropyridin-2-yl-oxy)-3,3-dimethyl-butan-2-oneHCID 1785160256-chloropyridin-2-ol

Product 1

HCID 204937241-((6-Chloropyridin-2-yl)oxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

33.8 g (0.2 mol) of 1,1-dichloro-3,3-dimethyl-butan-2-one, 26 g (0.2 mol) of 6-chloro-2-hydroxy-pyridine, 21 g (0.3 mol) of 1,2,4-triazole and 56 g (0.4 mol) of potassium carbonate were heated under reflux in 250 ml of acetone for 12 hours, while stirring. Thereafter, the mixture was allowed to cool, the salt which had precipitated was filtered off and the filtrate was concentrated in vacuo. Isopropanol was added to the oily residue, it being possible to isolate successively three crystal fractions. The first two contained mainly 1,1-bis-(1,2,4-triazol-1-yl)-3,3-dimethylbutan-2-one of melting point 157°-158° C. and 1,1-bis-(6-chloropyridin-2-yl-oxy)-3,3-dimethyl-butan-2-one of melting point 102°-104° C. 4 g of 1-(6-chloropyridin-2-yl-oxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one of melting point 102° C. were obtained from the third fraction.

Workup

  1. temperatureto cool
  2. customthe salt which had precipitated
  3. filtrationwas filtered off
  4. concentrationthe filtrate was concentrated in vacuo
  5. additionIsopropanol was added to the oily residue, it
  6. customto isolate successively three crystal fractions

Sources & evidence

ORD record
ord-aa6266b5fb384ae5aac373f69984a715
Source dataset
uspto-grants-1983_08
Patent number
US04396624

Reaction notes

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