Triethylamine → HCID 13389395, compound

HRID 1374891Notes

Reaction equation

HRID 1374891 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[C:3]#[CH:4].C(N(CC)CC)C.Cl[Si:15]([CH3:23])([CH3:22])[CH2:16][CH2:17][Si:18](Cl)([CH3:20])[CH3:19]>ClCCl>[CH3:5][C:2]([N:1]1[Si:18]([CH3:20])([CH3:19])[CH2:17][CH2:16][Si:15]1([CH3:23])[CH3:22])([CH3:6])[C:3]#[CH:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 763193-Butyn-2-amine, 2-methyl-HCID 835521,2-Bis(chlorodimethylsilyl)ethane

Product 1

HCID 13389395HCID 13389395, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
15 °C

Procedure

3-Amino-3-methylbutyne (commercially available as 90% aqueous solution; 16.6 g) was dissolved in dichloromethane (150 ml), dried over sodium sulphate and filtered to give a solution containing 14.9 g of amine. To the stirred solution of amine under an atmosphere of nitrogen at ambient temperature was added dry triethylamine (48.4 ml). 1,2-Bis-(chlorodimethylsilyl)ethane (38.98 g) in dichloromethane (100 ml) was then added dropwise, maintaining the reaction temperature at 15° C. by cooling. The mixture was stirred for 3 hours, the colourless solid, which had formed during the reaction, was filtered from solution and the filtrate was evaporated under reduced pressure to give a paste. The paste was extracted into hexane and refiltered. The filtrate was evaporated under reduced pressure and the oil obtained was distilled to give 1-(1,1-dimethyl-2-propynyl)-2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane, 21.5 g, b.p. 41° C. at 0.06 mm Hg pressure.

Workup

  1. dry with materialdried over sodium sulphate
  2. filtrationfiltered
  3. customto give a solution
  4. temperatureby cooling
  5. customthe colourless solid, which had formed during the reaction
  6. filtrationwas filtered from solution
  7. customthe filtrate was evaporated under reduced pressure
  8. customto give a paste
  9. extractionThe paste was extracted into hexane
  10. customThe filtrate was evaporated under reduced pressure
  11. customthe oil obtained
  12. distillationwas distilled

Sources & evidence

ORD record
ord-4b9c0da8e92a40649aa2228eb9098e32
Source dataset
uspto-grants-2007_01
Patent number
US07166621B2

Reaction notes

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