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

HRID 436029Notes

Reaction equation

HRID 436029 reaction equation
[CH3:1][Si:2]([CH3:5])([CH3:4])Cl.[C:6]1(=[O:12])[NH:10][C:9](=[O:11])[CH2:8][CH2:7]1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:1][Si:2]([CH3:5])([CH3:4])[N:10]1[C:6](=[O:12])[CH2:7][CH2:8][C:9]1=[O:11]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 11439Succinimide

Product 1

HCID 116654792,5-Pyrrolidinedione, 1-(trimethylsilyl)-Yield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

780 ml (6.1 moles) of trimethylchlorosilane were added with vigorous stirring over 2 hours to a mixture of 400 g (4 moles) of succinimide, 900 ml (6.5 moles) of triethylamine and 2700 ml of toluene and the mixture was refluxed with stirring for one hour and was then cooled to room temperature. The mixture was filtered and the filter was washed with one liter of toluene and one liter of petroleum ether (b.p = 40°-60° C). The combined filtrate and washings were concentrated to 700 ml and then distilled at reduced pressure to 573 g (3.4 moles -- 84% yield) of N-trimethylsilyl succinimide with a boiling point of 62° C at 0.33 mm Hg.

Workup

  1. temperaturethe mixture was refluxed
  2. filtrationThe mixture was filtered
  3. washthe filter was washed with one liter of toluene and one liter of petroleum ether (b.p = 40°-60° C)
  4. concentrationThe combined filtrate and washings were concentrated to 700 ml

Sources & evidence

ORD record
ord-2622620a1dca42ad80560f979461f04e
Source dataset
uspto-grants-1977_02
Patent number
US04007202

Reaction notes

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