tert-Octylamine → HCID 123239943, compound

HRID 2273157Notes

Reaction equation

HRID 2273157 reaction equation
Cl[SiH:2]1[N:6]([C:7]([CH3:10])([CH3:9])[CH3:8])[CH:5]=[CH:4][N:3]1[C:11]([CH3:14])([CH3:13])[CH3:12].[CH3:15][C:16]([NH-:23])([CH3:22])[CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19].[Li+].CC(N)(C)CC(C)(C)C.C([Li])CCC>CCCCCC>[C:11]([N:3]1[CH:4]=[CH:5][N:6]([C:7]([CH3:10])([CH3:9])[CH3:8])[SiH:2]1[NH:23][C:16]([CH3:22])([CH3:15])[CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 61017tert-OctylamineHCID 15769382HCID 15769382, compoundHCID 713346111,3-Di-tert-butyl-2-chloro-2,3-dihydro-1H-1,3,2-diazasiloleHCID 178418339Butyllithium

Product 1

HCID 123239943HCID 123239943, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent3×

Procedure

In an argon atmosphere, a solution obtained by dissolving 5.14 g (22.1 mmol) of Si(tBuNCHCHNtBu)(H)Cl in 10 mL of hexane was added to a lithium(1,1,3,3-tetramethylbutylamide) solution prepared by adding 10 mL of hexane and 2.94 g (22.8 mmol) of 1,1,3,3-tetramethylbutylamine to 13.8 mL (22.8 mmol) of a hexane solution (concentration: 1.65 mol/L) of butyllithium and stirring the mixture at room temperature for 14 hours, and the resulting mixture was stirred at room temperature for 24 hours. Insoluble matters produced were separated by filtration, and the solvent was removed by distillation from the filtrate under atmospheric pressure. The obtained residue was sublimated (heating temperature: 180° C./64 Pa) to obtain 1,3-di-tert-butyl-2-(1,1,3,3-tetramethylbutyl)amino-1,3-diaza-2-silacyclopent-4-ene (Si(tBuNCHCHNtBu)(H)NHtOct) as a white solid (yielded amount: 5.85 g, yield: 81%).

Workup

  1. customIn an argon atmosphere, a solution obtained
  2. customprepared
  3. stirringthe resulting mixture was stirred at room temperature for 24 hours
  4. customInsoluble matters produced
  5. customwere separated by filtration
  6. customthe solvent was removed by distillation from the filtrate under atmospheric pressure
  7. temperature(heating temperature: 180° C./64 Pa)
  8. customto obtain

Sources & evidence

ORD record
ord-496f0ddc501243c58a879be5c187ea40
Source dataset
uspto-grants-2015_09
Patent number
US09120825B2

Reaction notes

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