Methanol → Methyl 1-(3-pyridylmethyl)-5-(1,3-dithiol-2-ylidene)-4,6-dioxopiperidine-3-carboxylate

HRID 977962Notes

Reaction equation

HRID 977962 reaction equation
[Na].CO.[S:4]1[CH:8]=[CH:7][S:6][C:5]1=[C:9]([C:15](=[O:30])[N:16]([CH2:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:10](OCC)=[O:11]>C1C=CC=CC=1>[N:26]1[CH:27]=[CH:28][CH:29]=[C:24]([CH2:23][N:16]2[C:15](=[O:30])[C:9](=[C:5]3[S:4][CH:8]=[CH:7][S:6]3)[C:10](=[O:11])[CH:18]([C:19]([O:21][CH3:22])=[O:20])[CH2:17]2)[CH:25]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 5360545SodiumHCID 54216764ethyl 2-(1,3-dithiol-2-ylidene)-2-[N-(3-pyridylmethyl)-N-(methoxycarbonylethyl)carbamoyl]acetate

Product 1

HCID 13934863Methyl 1-(3-pyridylmethyl)-5-(1,3-dithiol-2-ylidene)-4,6-dioxopiperidine-3-carboxylateYield 51%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Sodium (156 mg) is added to methanol (5ml) and thereto is added a solution of ethyl 2-(1,3-dithiol-2-ylidene)-2-[N-(3-pyridylmethyl)-N-(methoxycarbonylethyl)carbamoyl]acetate (2.21 g) in benzene (35 ml). The mixture is refluxed for 3 hours, and distilled to remove the solvent. The residue is dissolved in ethyl acetate, and the solution is washed with water, dried and then distilled to remove the solvent. The residue is recrystallized from a mixture of ethyl acetate and n-hexane to give methyl 1-(3-pyridylmethyl)-5-(1,3-dithiol-2-ylidene)-4,6-dioxopiperidine-3-carboxylate (1.0 g, 51%) as pale yellow needles, m.p. 111°-114° C.

Workup

  1. temperatureThe mixture is refluxed for 3 hours
  2. distillationdistilled
  3. customto remove the solvent
  4. dissolutionThe residue is dissolved in ethyl acetate
  5. washthe solution is washed with water
  6. customdried
  7. distillationdistilled
  8. customto remove the solvent
  9. customThe residue is recrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-341b238e83d549d2a2defab6dbedd54c
Source dataset
uspto-grants-1987_05
Patent number
US04663319

Reaction notes

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