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Phenylacetylene → Silanediamine, N,N,N',N'-tetraethyl-1,1-bis(phenylethynyl)-

HRID 612975
Notes
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Reaction equation

HRID 612975 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)#[CH:7].Cl[Si:15](Cl)([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[N:16]([CH2:19][CH3:20])[CH2:17][CH3:18].[Cu](C#N)C#N>O1CCCC1>[CH2:17]([N:16]([Si:15]([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])([C:7]#[C:6][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:1]#[C:2][C:3]1[CH:4]=[CH:4][CH:3]=[CH:2][CH:1]=1)[CH2:19][CH3:20])[CH3:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 10821PhenylacetyleneHCID 131337371,1-Dichloro-N,N,N',N'-tetraethylsilanediamineHCID 178418260HCID 178418260, compoundHCID 178418339Butyllithium

Product 1

HCID 11760549Silanediamine, N,N,N',N'-tetraethyl-1,1-bis(phenylethynyl)-Yield 93%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

1.6 N normal butyl lithium 205 ml was dropwise added to a solution comprising 33 ml of ethynylbenzene and 300 ml of tetrahydrofuran (hereinafter abbreviated as THF) at 0° C. under nitrogen gas flow, and stirring was continued for 1.5 hour. Dichlorobis(diethylamino)silane 36.5 g and 672 mg of copper cyanide were added to the resulting solution, and stirring was continued at room temperatures for 20 minutes to carry out the reaction. Solid matters precipitated in the reaction liquid were removed by filtering, and then the filtrate was concentrated. Water was added to this concentrate to extract the product with ether. This ether extraction layer was washed with water and then dried on magnesium sulfate. An ether component of this liquid was distilled off, and then the residue was refined by distillation to obtain 52 g of bis(diethylamino)-bis(phenyethynyl)silane. The yield was 93%.

Workup

  1. customat 0° C.
  2. stirringstirring
  3. waitwas continued at room temperatures for 20 minutes
  4. customthe reaction
  5. customSolid matters precipitated in the reaction liquid
  6. customwere removed
  7. filtrationby filtering
  8. concentrationthe filtrate was concentrated
  9. additionWater was added to
  10. concentrationthis concentrate
  11. extractionto extract the product with ether
  12. extractionThis ether extraction layer
  13. washwas washed with water
  14. customdried on magnesium sulfate
  15. distillationAn ether component of this liquid was distilled off
  16. distillationthe residue was refined by distillation

Sources & evidence

ORD record
ord-a18b6cfd517f4267828a5bcf84c851cf
Source dataset
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06005128

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes