Sodium hydride → 1-Ethyl-3-(1,3-dithiol-2-ylidene)-2,4-dioxopiperidine

HRID 977940Notes

Reaction equation

HRID 977940 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][C:4]1=[O:10])[CH3:2].[H-].[Na+].[I-].CS[C:16]1[S:20][CH:19]=[CH:18][S+:17]=1>CN(C)C=O>[CH2:1]([N:3]1[CH2:8][CH2:7][C:6](=[O:9])[C:5](=[C:16]2[S:20][CH:19]=[CH:18][S:17]2)[C:4]1=[O:10])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 137841191-Ethylpiperidine-2,4-dioneHCID 19751531(2H-1,3-Dithiol-2-ylidene)(methyl)sulfanium iodide

Product 1

HCID 136065471-Ethyl-3-(1,3-dithiol-2-ylidene)-2,4-dioxopiperidineYield 66.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1-Ethyl-2,4-dioxopiperidine (1.06 g) is dissolved in N,N-dimethylformamide (50 ml), and the solution is added dropwise to a suspension of sodium hydride (60% dispersion in oil, 332 mg) in N,N-dimethylformamide (50 ml) under ice-cooling. The mixture is stirred for 20 minutes, and thereto is added 2-methylthio-1,3-dithiolium iodide (1.89 g). After stirring at room temperature overnight, the reaction mixture is poured onto water and extracted with ethyl acetate. The extract is washed with water, dried and distilled to remove the solvent. The residue is purified by silica gel column chromatography (developer: ethyl acetate) and then recrystallized from ethyl acetate-isopropyl ether to give 1-ethyl-3-(1,3-dithiol-2-ylidene)-2,4-dioxopiperidine (1.10 g) as pale yellow needles. m.p. 114.5°-117° C.

Workup

  1. temperaturecooling
  2. stirringAfter stirring at room temperature overnight
  3. additionthe reaction mixture is poured onto water
  4. extractionextracted with ethyl acetate
  5. washThe extract is washed with water
  6. customdried
  7. distillationdistilled
  8. customto remove the solvent
  9. customThe residue is purified by silica gel column chromatography (developer: ethyl acetate)
  10. customrecrystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-de4c72ee6b95497b9fdc796c9f679983
Source dataset
uspto-grants-1987_05
Patent number
US04663319

Reaction notes

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