Acetonitrile → HCID 53671371, compound

HRID 522344Notes

Reaction equation

HRID 522344 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-c75741b5b60f4f81994fc61a945b5dd2
Source dataset
uspto-grants-2016_05
Patent number
US09329184B2

Reaction notes

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