Acetonitrile → HCID 53671371, compound

HRID 1755494Notes

Reaction equation

HRID 1755494 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:9]=[C:10]([CH:12]=[CH:13][CH:14]=1)[NH2:11].[CH2:15](Br)[CH:16]=[CH2:17].[C:19](#N)[CH3:20]>>[Br:7][C:8]1[CH:9]=[C:10]([CH:12]=[CH:13][CH:14]=1)[N:11]([CH2:1][CH:19]=[CH2:20])[CH2:15][CH:16]=[CH2:17]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 115623-Bromoaniline

Product 1

HCID 53671371HCID 53671371, compoundYield 85%

Conditions

Temperature
80 °C

Procedure

Potassium carbonate (22.0 g, 159 mmol) was suspended in acetonitrile, 3-bromoaniline (8.71 mL, 80.0 mmol) and allyl bromide (23.7 mL, 280 mmol) were added to the suspension, and the mixture was stirred at 80° C. for 14 hours. The reaction mixture was cooled to room temperature, then filtered through Celite, and sufficiently washed with ethyl acetate. The solvent was removed, and then the residue was purified by column chromatography (silica gel, ethyl acetate/hexane (1/40)) to obtain 3-bromo-N,N-diallylaniline (17.1 g, 67.9 mmol, yield 85%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered through Celite
  3. washsufficiently washed with ethyl acetate
  4. customThe solvent was removed
  5. customthe residue was purified by column chromatography (silica gel, ethyl acetate/hexane (1/40))

Sources & evidence

ORD record
ord-2bfabb70b9d54e71b86ddb4efb9fcc09
Source dataset
uspto-grants-2015_10
Patent number
US09170266B2

Reaction notes

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