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

HRID 977941Notes

Reaction equation

HRID 977941 reaction equation
[H-].[Na+].[CH2:3]([N:10]1[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][C:11]1=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[I-].CS[C:21]1[S:25][CH:24]=[CH:23][S+:22]=1>O1CCCC1>[CH2:3]([N:10]1[CH2:15][CH2:14][C:13](=[O:16])[C:12](=[C:21]2[S:25][CH:24]=[CH:23][S:22]2)[C:11]1=[O:17])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 19751531(2H-1,3-Dithiol-2-ylidene)(methyl)sulfanium iodideHCID 224955411-Benzylpiperidine-2,4-dione

Product 1

HCID 136065591-Benzyl-3-(1,3-dithiol-2-ylidene)-2,4-dioxopiperidineYield 87.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% dispersion in oil) (80 mg) is suspended in tetrahydrofuran (10 ml), and thereto are added 1-benzyl-2,4-dioxopiperidine (200 mg) and 2-methylthio-1,3-dithiolium iodide (273 mg). The mixture is stirred at room temperature for 30 minutes. The reaction mixture is poured onto water and extracted with chloroform. The extract is washed with a saturated sodium chloride solution, dried and then distilled to remove the solvent. The residue is purified by silica gel column chromatography (solvent; ethyl acetate:n-hexane=1:1) and recrystallized from isopropyl alcohol to give 1-benzyl-3-(1,3-dithiol-2-ylidene)-2,4-dioxopiperidine (262 mg, 87.8%) as pale yellow needles, m.p. 122°-124° C.

Workup

  1. additionThe reaction mixture is poured onto water
  2. extractionextracted with chloroform
  3. washThe extract is washed with a saturated sodium chloride solution
  4. customdried
  5. distillationdistilled
  6. customto remove the solvent
  7. customThe residue is purified by silica gel column chromatography (solvent; ethyl acetate:n-hexane=1:1)
  8. customrecrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-5df2db783bb24444a96293ab58b974af
Source dataset
uspto-grants-1987_05
Patent number
US04663319

Reaction notes

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