Ammonia → 2,4-Imidazolidinedione, 5,5-dimethyl-1,3-bis(trimethylsilyl)-

HRID 435199Notes

Reaction equation

HRID 435199 reaction equation
C[Si](C)(C)[NH:3][Si:4]([CH3:7])([CH3:6])[CH3:5].[CH3:10][C:11]1([CH3:18])[NH:15][C:14](=[O:16])N[C:12]1=[O:17].N>S1(C2C(=CC=CC=2)C(=O)N1)(=O)=O.C1(C)C=CC=CC=1>[CH3:5][Si:4]([CH3:7])([CH3:6])[N:15]1[C:11]([CH3:18])([CH3:10])[C:12](=[O:17])[N:3]([Si:4]([CH3:5])([CH3:6])[CH3:7])[C:14]1=[O:16]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 6491DimethylhydantoinHCID 13838Hexamethyldisilazane3×

Product 1

HCID 5751422,4-Imidazolidinedione, 5,5-dimethyl-1,3-bis(trimethylsilyl)-Yield 152.6%

Reagents, catalysts & solvents 2

HCID 5143SaccharinCatalystHCID 1140TolueneSolvent

Procedure

80 ml of hexamethyldisilazane (0.38 mole) were added over 30 minutes to a refluxing suspension of 50 ml of toluene, 40 mg (0.22 mmole) of saccharin and 38.45 g (0.30 mole) of 5,5-dimethylhydantoin and evolution of ammonia started immediately. When half of the hexamethyldisilazane had been added, all solids had gone into solution and after the addition of the hexamethyldisilazane, reflux was continued for 1 hour. Toluene was distilled off and the residue was vacuum dried at 45° C. to obtain 79.0 g (97%) of 1,3-bis-(trimethylsilyl)-5,5-dimethylhydantoin melting at 46°-49° C. According to NMR analysis, the purity of the compound was 91%.

Workup

  1. temperaturereflux
  2. distillationToluene was distilled off
  3. customdried at 45° C.

Sources & evidence

ORD record
ord-56c5abe9da744f2d8fb3905cfbb1fd19
Source dataset
uspto-grants-1983_08
Patent number
US04400509

Reaction notes

Loading…