1H-1,2,4-Triazole → 3,3-Dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone

HRID 1578108Notes

Reaction equation

HRID 1578108 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].[CH3:12][C:13]([C:16]([CH2:18]Cl)=[O:17])([CH3:15])[CH3:14]>CC(C)=O>[CH3:12][C:13]([CH3:15])([CH3:14])[C:16](=[O:17])[CH2:18][N:1]1[CH:5]=[N:4][CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 835721-Chloropinacolone

Product 1

HCID 1008773,3-Dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanoneYield 72%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

138 g (2 mol) of 1,2,4-triazole were added in portions to 276.4 g (2 mol) of ground potassium carbonate and 269.2 g (2 mol) of α-chloropinacolin in 500 ml of acetone at room temperature, during which the internal temperature rose to the boiling point. The mixture was stirred under reflux for 5 hours and then cooled to room temperature. The reaction mixture was filtered and the filtrate was concentrated by distilling off the solvent in vacuo. After adding benzine, the oily residue crystallized. 240.8 g (72% of theory) of 3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one of melting point 62°-64° C. were obtained.

Workup

  1. temperatureunder reflux for 5 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. distillationby distilling off the solvent in vacuo
  5. additionAfter adding benzine
  6. customthe oily residue crystallized

Sources & evidence

ORD record
ord-43a8cd4097014d7ba316bdbbfe25697a
Source dataset
uspto-grants-1981_09
Patent number
US04291047

Reaction notes

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