Sodium hydride → 4-Methyl-1-(3-oxooctyl)-1,2,4-triazolidine-3,5-dione

HRID 1462389Notes

Reaction equation

HRID 1462389 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[NH:5][NH:4][C:3]1=[O:8].[H-].[Na+].[CH2:11]=[CH:12][C:13](=[O:19])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>CN(C)C=O.C(OCC)(=O)C>[CH3:1][N:2]1[C:6](=[O:7])[NH:5][N:4]([CH2:11][CH2:12][C:13](=[O:19])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:3]1=[O:8]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 613461-Octen-3-oneHCID 1777354-Methyl-1,2,4-triazolidine-3,5-dione

Product 1

HCID 129399964-Methyl-1-(3-oxooctyl)-1,2,4-triazolidine-3,5-dioneYield 54.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-methyl-1,2,4-triazolidine-3,5-dione (5.75 g, 0.05 mol) in dry dimethylformamide (40 ml) stirred at 75° under a nitrogen atmosphere was added portionwise sodium hydride (1.575 g, 0.055 mol, as an 80% dispersion in mineral oil) and the resultant solution stirred at 75° for 0.5 hr. To this solution was added oct-1-en-3-one (6.57 g, 0.055 mol) dropwise in dimethylformamide (20 ml) and the solution heated with stirring for 48 hr at 75°. The reaction mixture was then cooled, taken up in ethyl acetate (100 ml) and poured into ice-cold 5N aqueous hydrochloric acid (200 ml). The aqueous layer was separated and extracted with ethyl acetate (4×100 ml). The combined extracts were washed with 5N aqueous hydrochloric acid, water and then brine, then dried (Na2SO4), filtered and the solvent removed by evaporation in vacuo, to leave a gum (6.55 g). This was chromatographed on silica gel (Merck, Kieselgel 60) with a packing ratio of 1:20 with chloroform as eluant, to afford the triazolidine-3,5-dione (4.61 g) as a gum, which later solidified. (In subsequent preparations the crude material from the reaction mixture could be triturated with hexane to induced crystallisation), m.p. 76°-8°.

Workup

  1. temperaturethe solution heated
  2. temperatureThe reaction mixture was then cooled
  3. customThe aqueous layer was separated
  4. extractionextracted with ethyl acetate (4×100 ml)
  5. washThe combined extracts were washed with 5N aqueous hydrochloric acid, water
  6. dry with materialbrine, then dried (Na2SO4)
  7. filtrationfiltered
  8. customthe solvent removed by evaporation in vacuo

Sources & evidence

ORD record
ord-4932fc87455243d3bd187daca858aec0
Source dataset
uspto-grants-1984_07
Patent number
US04460595

Reaction notes

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