Saccharin → 2,5-Pyrrolidinedione, 1-(trimethylsilyl)-

HRID 435196Notes

Reaction equation

HRID 435196 reaction equation
[CH3:1][Si:2]([CH3:9])([CH3:8])[NH:3][Si](C)(C)C.[C:10]1(=[O:16])N[C:13](=[O:15])[CH2:12][CH2:11]1.S1(C2C(=CC=CC=2)C(=O)N1)(=O)=O>C1(C)C=CC=CC=1>[CH3:1][Si:2]([CH3:9])([CH3:8])[N:3]1[C:13](=[O:15])[CH2:12][CH2:11][C:10]1=[O:16]

Participants

5

Reactant 3

HCID 5143SaccharinHCID 11439SuccinimideHCID 13838Hexamethyldisilazane

Product 1

HCID 116654792,5-Pyrrolidinedione, 1-(trimethylsilyl)-Yield 120,823.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

31.5 ml of hexamethyldisilazane (0.15 mmole) were added to a refluxing suspension of a mixture of 50 ml of toluene and 19.80 g (0.20 mole) of succinimide and 458 mg of saccharin (2.5 mmoles) and refluxing was continued for 2 hours. Fifteen minutes after the addition of the silylating agent, a clear, light yellow solution was obtained which turned brown when refluxing was continued. The reaction mixture was cooled, filtered and after evaporation of the solvent, the residue was vacuum distilled to obtain 31.04 g (90.8%) of N-trimethylsilylsuccinimide boiling at 86°-88° C. at 1.3 mm Hg.

Workup

  1. temperaturerefluxing
  2. additionFifteen minutes after the addition of the silylating agent
  3. customa clear, light yellow solution was obtained which
  4. temperaturerefluxing
  5. temperatureThe reaction mixture was cooled
  6. filtrationfiltered
  7. customafter evaporation of the solvent
  8. distillationdistilled

Sources & evidence

ORD record
ord-e5956fc8cb834ccca62a044f337ce71b
Source dataset
uspto-grants-1983_08
Patent number
US04400509

Reaction notes

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