Chlorotrimethylsilane → HCID 131716947, compound

HRID 1090834Notes

Reaction equation

HRID 1090834 reaction equation
[CH:1]#[C:2][C:3]([NH2:6])([CH3:5])[CH3:4].C(N(CC)CC)C.[CH3:14][Si:15]([CH3:18])([CH3:17])Cl>O1CCCC1>[CH:1]#[C:2][C:3]([NH:6][Si:15]([CH3:18])([CH3:17])[CH3:14])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 6397Chlorotrimethylsilane2×HCID 8471TriethylamineHCID 763193-Butyn-2-amine, 2-methyl-2×

Product 1

HCID 131716947HCID 131716947, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 5000 ml flask were combined 250 g of commercial HC≡CCMe2NH2, 581.8 g of triethylamine, and 1637.5 g of tetrahydrofuran solvent. The flask and contents were cooled at 17° and addition of 625.5 g of trimethylchlorosilane begun with rapid stirring under nitrogen. The addition was completed in 90 min, followed by stirring for 85 min. Analysis by gas chromatography (GC) showed a small amount of HC≡CCMe2NH2, which was converted to product by an additional 53.4 g of trimethylchlorosilane. Reaction mixture was pressure-filtered and the solids triturated with fresh tetrahydrofuran and refiltered. The organic solutions were combined and distilled, providing the desired product, HC≡CCMe2NHSiMe3, as a liquid boiling at 135° at atmospheric pressure. Its structure was confirmed by NMR analysis.

Workup

  1. customIn 5000 ml flask were combined
  2. temperatureThe flask and contents were cooled at 17°
  3. additionThe addition
  4. stirringby stirring for 85 min
  5. customReaction mixture
  6. filtrationwas pressure-filtered
  7. customthe solids triturated with fresh tetrahydrofuran
  8. distillationdistilled

Sources & evidence

ORD record
ord-59f597711b4d45e2897bbb5e33723c98
Source dataset
uspto-grants-1992_01
Patent number
US05082962

Reaction notes

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