Chlorotrimethylsilane → N,N'-Dimethyl-N,N'-bis(trimethylsilyl)urea

HRID 1614277Notes

Reaction equation

HRID 1614277 reaction equation
[CH3:1][NH:2][C:3]([NH:5][CH3:6])=[O:4].Cl[Si:8]([CH3:11])([CH3:10])[CH3:9]>C(N(CC)CC)C>[CH3:9][Si:8]([CH3:11])([CH3:10])[N:2]([CH3:1])[C:3]([N:5]([Si:8]([CH3:11])([CH3:10])[CH3:9])[CH3:6])=[O:4]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 7293N,N'-Dimethylurea

Product 1

HCID 12479153N,N'-Dimethyl-N,N'-bis(trimethylsilyl)urea

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

1,3-dimethylurea (44.0 g, 0.5 mole) and triethylamine (250 mls) were charged to a stirred reaction vessel purged with dry nitrogen. The mixture was stirred for 5 minutes and then chlorotrimethylsilane (167.5 mls, 1.32 moles) was added resulting in the formation of a white precipitate. The resulting reaction mixture was stirred for a further 24 hours at ambient temperature after which it was filtered under a nitrogen atmosphere. The filter cake was washed with dry toluene and the combined organics filtrate was distilled at atmospheric pressure under a nitrogen atmosphere. The residual organics were subjected to fractional distillation at a pressure of 8 mmHg. The fraction distilling at 86° to 88° C. was the required initiator.

Workup

  1. custompurged with dry nitrogen
  2. customresulting in the formation of a white precipitate
  3. customThe resulting reaction mixture
  4. stirringwas stirred for a further 24 hours at ambient temperature after which it
  5. filtrationwas filtered under a nitrogen atmosphere
  6. washThe filter cake was washed with dry toluene
  7. distillationthe combined organics filtrate was distilled at atmospheric pressure under a nitrogen atmosphere
  8. distillationThe residual organics were subjected to fractional distillation at a pressure of 8 mmHg
  9. distillationThe fraction distilling at 86° to 88° C.

Sources & evidence

ORD record
ord-51c3e08149ca45bf8c72b0f2bd997f47
Source dataset
uspto-grants-1993_03
Patent number
US05196489

Reaction notes

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