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

HRID 893900Notes

Reaction equation

HRID 893900 reaction equation
[C:1]1(=[O:7])[NH:5][C:4](=[O:6])[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:15][Si:16]([CH3:19])([CH3:18])Cl>C1(C)C=CC=CC=1>[CH3:15][Si:16]([CH3:19])([CH3:18])[N:5]1[C:4](=[O:6])[CH2:3][CH2:2][C:1]1=[O:7]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 11439Succinimide

Product 1

HCID 116654792,5-Pyrrolidinedione, 1-(trimethylsilyl)-

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 400 g (4 moles) of succinimide and 900 ml of triethylamine in 2700 ml of toluene 780 ml of trimethylchlorosilane were added in two hours with vigorous stirring. After refluxing and stirring for an additional hour the mixture was allowed to cool to room temperature. The precipitate was filtered off, washed with 1 l of toluene and 1 l of light petrol (40°-60° C.) and the combined filtrate and washings concentrated to about 700 ml. N-trimethylsilylsuccinimide was isolated by distillation at diminished pressure. The yield was 573 g (3.35 moles) or 83.5%; boiling point 62° C./0.3 mm Hg.

Workup

  1. temperatureAfter refluxing
  2. filtrationThe precipitate was filtered off
  3. washwashed with 1 l of toluene and 1 l of light petrol (40°-60° C.)
  4. concentrationthe combined filtrate and washings concentrated to about 700 ml

Sources & evidence

ORD record
ord-8668dde6452545ec8d766381655a7a35
Source dataset
uspto-grants-1981_08
Patent number
US04282145

Reaction notes

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