Dimethylamine → HCID 12532901, compound

HRID 1741614Notes

Reaction equation

HRID 1741614 reaction equation
[C:1]([C:4]1[O:5][CH:6]=[CH:7][CH:8]=1)(=O)[CH3:2].[CH3:9][NH:10][CH3:11]>C1C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[CH3:9][N:10]([CH3:11])[C:1]([C:4]1[O:5][CH:6]=[CH:7][CH:8]=1)=[CH2:2]

Participants

5

Reactant 2

HCID 674DimethylamineHCID 145052-Acetylfuran

Product 1

HCID 12532901HCID 12532901, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 241BenzeneSolvent2×

Procedure

To a solution of 55 g of 2-acetylfuran and 193 g of dimethylamine in 1 liter of dry benzene, stirred at 3° under nitrogen, is added dropwise a solution of 31 mL of titanium tetrachloride in 100 mL benzene over 45 minutes. The mixture is stirred for a further 3 hours at 3°, then at ambient temperature overnight. The brown reaction mixture is filtered through a medium frit glass funnel under nitrogen, and the filtered solids are washed with dry benzene. The combined filtrates are concentrated in vacuo to give the desired enamine as an oil.

Workup

  1. customat ambient temperature
  2. customovernight
  3. filtrationThe brown reaction mixture is filtered through a medium frit glass funnel under nitrogen
  4. washthe filtered solids are washed with dry benzene
  5. concentrationThe combined filtrates are concentrated in vacuo

Sources & evidence

ORD record
ord-4364eb3c46a048869b13592edcbd29e3
Source dataset
uspto-grants-1994_08
Patent number
US05334576

Reaction notes

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