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

HRID 977947Notes

Reaction equation

HRID 977947 reaction equation
[H-].[Na+].[S:3]1[CH:7]=[CH:6][S:5][C:4]1=[C:8]1[C:13](=[O:14])[CH2:12][CH2:11][NH:10][C:9]1=[O:15].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O>[CH2:16]([N:10]1[CH2:11][CH2:12][C:13](=[O:14])[C:8](=[C:4]2[S:5][CH:6]=[CH:7][S:3]2)[C:9]1=[O:15])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 136065623-(1,3-Dithiol-2-ylidene)-2,4-dioxopiperidine

Product 1

HCID 136065591-Benzyl-3-(1,3-dithiol-2-ylidene)-2,4-dioxopiperidineYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (60% dispersion in oil) (47 mg) is suspended in N,N-dimethylformamide (2 ml), and to the suspension is added dropwise a solution of 3-(1,3-dithiol-2-ylidene)-2,4-dioxopiperidine (200 mg) in N,N-dimethylformamide (16 ml). The mixture is stirred for 10 minutes and thereto is added benzyl bromide (0.12 ml), and the mixture is further stirred for 1 hour. After the reaction, the reaction mixture is distilled to remove the solvent under reduced pressure and the residue is dissolved in chloroform. The chloroform solution is washed with an aqueous saturated sodium chloride solution, 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 (176 mg, 62%) as pale yellow needles. m.p. 122°-124° C.

Workup

  1. stirringthe mixture is further stirred for 1 hour
  2. customAfter the reaction
  3. distillationthe reaction mixture is distilled
  4. customto remove the solvent under reduced pressure
  5. dissolutionthe residue is dissolved in chloroform
  6. washThe chloroform solution is washed with an aqueous saturated sodium chloride solution
  7. customdried
  8. distillationdistilled
  9. customto remove the solvent
  10. customThe residue is recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-6b1b8a3f5a2f4561ab3fb83a0b95aabd
Source dataset
uspto-grants-1987_05
Patent number
US04663319

Reaction notes

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