Dimethylamine → HCID 18783380, compound

HRID 1421139Notes

Reaction equation

HRID 1421139 reaction equation
[CH3:1][NH:2][CH3:3].[CH3:4][CH:5]1[C:9]([Si:10](Cl)([CH3:12])[CH3:11])=[C:8]([CH3:14])[C:7]([CH3:15])=[C:6]1[CH3:16].C1COCC1>>[CH3:1][N:2]([Si:10]([CH:9]1[C:5]([CH3:4])=[C:6]([CH3:16])[C:7]([CH3:15])=[C:8]1[CH3:14])([CH3:11])[CH3:12])[CH3:3]

Participants

4

Reactant 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 15878593HCID 15878593, compound

Product 1

HCID 18783380HCID 18783380, compound

Conditions

Temperature
15 °C

Procedure

A 250 mL roundbottom flask equipped with a condenser, stirrer, thermometer and dropping funnel with nitrogen inlet was charged with 100 mL of dimethylamine solution (2.0 M in THF, 0.20 mol) and cooled to 15° C. A solution of tetramethylcyclopenta-dienyldimethylsilylchloride in THF (10.1 g in 30 mL THF, 47 mmol) was added and the solution stirred for 16 hours allowing the temperature of the reaction mixture to rise to room temperature. A precipitate was filtered off and the solvent evaporated. The remaining residue was distilled at sub-atmospheric pressure (2.6 mbar) at 80-81° C. to obtain [(N,N-dimethylamino)dimethylsilyl]tetramethyl-cyclopentadiene (4.2 g). The product was characterized by GC, GC-MS, 13C and 1H NMR.

Workup

  1. customA 250 mL roundbottom flask equipped with a condenser, stirrer
  2. customto rise to room temperature
  3. filtrationA precipitate was filtered off
  4. customthe solvent evaporated
  5. distillationThe remaining residue was distilled at sub-atmospheric pressure (2.6 mbar) at 80-81° C.

Sources & evidence

ORD record
ord-04bfcd8ae0824c1784002c267ecb3ed1
Source dataset
uspto-grants-2000_06
Patent number
US06072067

Reaction notes

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