Carbon Disulfide → 1-Benzyl-3-(1,3-dithiol-2-ylidene)-2,4-dioxopiperidine

HRID 977950Notes

Reaction equation

HRID 977950 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.[C:18](=[S:20])=[S:19].Cl/[CH:22]=[CH:23]\Cl>CS(C)=O>[CH2:3]([N:10]1[CH2:15][CH2:14][C:13](=[O:16])[C:12](=[C:18]2[S:20][CH:23]=[CH:22][S:19]2)[C:11]1=[O:17])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 24758Sodium hydrideHCID 643833cis-1,2-DichloroethyleneHCID 224955411-Benzylpiperidine-2,4-dione

Product 1

HCID 136065591-Benzyl-3-(1,3-dithiol-2-ylidene)-2,4-dioxopiperidine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

Sodium hydride (60% despersion in oil) (432 mg) is suspended in dimethylsulfoxide (10 ml), and to the suspension is added dropwise a solution of 1-benzyl-2,4-dioxopiperidine (1.0 g) and carbon disulfide (0.33 ml) in dimethylsulfoxide (20 ml). The mixture is stirred for 2 hours, and thereto is added dropwise a solution of cis-1,2-dichloroethylene (0.42 ml) in dimethylsulfoxide (5 ml). The mixture is stirred at room temperature for 1.5 hour and further at 50° C. for 1 hour. The reaction mixture is poured onto water and extracted with benzene. The extract is washed with water, dried and then distilled to remove the solvent. The residue is recrystallized from isopropyl alcohol to give 1-benzyl-3-(1,3-dithiol-2-ylidene)-2,4- dioxopiperidine (486 mg) as pale yellow needles. m.p. 122°-124° C.

Workup

  1. stirringThe mixture is stirred at room temperature for 1.5 hour and further at 50° C. for 1 hour
  2. additionThe reaction mixture is poured onto water
  3. extractionextracted with benzene
  4. washThe extract is washed with water
  5. customdried
  6. distillationdistilled
  7. customto remove the solvent
  8. customThe residue is recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-cb7aef7f2e6e4f0a93b9032debeec418
Source dataset
uspto-grants-1987_05
Patent number
US04663319

Reaction notes

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