1H-1,2,4-Triazole → HCID 22163855, compound

HRID 1087773Notes

Reaction equation

HRID 1087773 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[N:6][CH:5]=[N:4]1.[H][H].[CH3:10][C:11]([CH3:21])([CH2:15]OS(C)(=O)=O)[C:12](=[O:14])[CH3:13]>CN(C)C=O.O>[CH3:10][C:11]([CH3:21])([CH2:15][N:3]1[CH:7]=[N:6][CH:5]=[N:4]1)[C:12](=[O:14])[CH3:13]

Participants

7

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 10878028HCID 10878028, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22163855HCID 22163855, compoundYield 86.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

In the course of 3 hours, 60 g (2 mols of sodium hydride (80% strength in paraffin oil) are added to a solution of 138 g (2 mols of 1,2,4-triazole in 1,600 ml of absolute dimethylformamide, with vigorous evolution hydrogen. The mixture is stirred for a further 30 minutes at room temperature. 388 g (2 mols of 3,3-dimethyl -4-[(methylsulphonyl)oxy]-2-butanone are then added dropwise in the course of 15 minutes. The reaction mixture is then stirred for 16 hours at 95° C. 100 ml of water are firstly added carefully to the reaction mixture, and the mixture is then poured into 4 1 of water. The mixture is extracted six times with dichloromethane. The combined organic phases are washed once with plenty of water, dried over sodium sulphate and concentrated under a high vacuum. After column chromatography (silica gel; dichloromethane/ethyl acetate=1:1), 290 g (86.8% of 3,3-dimethyl -4-(1,2,4-triazol-1-yl)-2-butanone are obtained as an oil with a content of 97% after GC.

Workup

  1. stirringThe reaction mixture is then stirred for 16 hours at 95° C
  2. extractionThe mixture is extracted six times with dichloromethane
  3. washThe combined organic phases are washed once with plenty of water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under a high vacuum

Sources & evidence

ORD record
ord-0b2d568d9ed5457683ac4fb060f8619c
Source dataset
uspto-grants-1990_10
Patent number
US04960781

Reaction notes

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