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

HRID 435197Notes

Reaction equation

HRID 435197 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.N.O>ClCCl>[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

6

Reactant 4

HCID 222Ammonia4×HCID 962WaterHCID 11439SuccinimideHCID 13838Hexamethyldisilazane

Product 1

HCID 116654792,5-Pyrrolidinedione, 1-(trimethylsilyl)-Yield 119.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

15.6 ml (0.075 mole) of hexamethyldisilazane were added dropwise over a few minutes to a refluxing suspension of 9.90 g (0.1 mole) of succinimide and 0.24 g (0.5 mmole) of di-4-nitrophenyl N-4-toluenesulfonyl-phosphoramidate in 50 ml of dichloromethane and a stream of nitrogen was led over the reaction mixture to pass the ammonia evolved into water. The progress of the reaction was established by titration of the ammonia evolved and it was found that after refluxing for 1.5 hours, the production of ammonia was completed. 90% of the theoretical amount of ammonia had been evolved and refluxing was continued for another 2 hours. Then the solvent was removed by distillation at normal pressure and fractionation under reduced pressure yielded 15.36 g (89.8%) of N-trimethylsilylsuccinimide boiling at 118°-119° C. at 18 mm Hg and nD 25=1.4745.

Workup

  1. temperaturethat after refluxing for 1.5 hours
  2. temperaturerefluxing
  3. customThen the solvent was removed by distillation at normal pressure and fractionation under reduced pressure

Sources & evidence

ORD record
ord-7c3bea7ec90b438ebe09a2a450737332
Source dataset
uspto-grants-1983_08
Patent number
US04400509

Reaction notes

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