Benzaldehyde → HCID 178505640, compound

HRID 1397724Notes

Reaction equation

HRID 1397724 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].S([O-])([O-])(=O)=O.[Mg+2].[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CC1C=CC(S(O)(=O)=O)=CC=1>CCOCC>[CH:15](=[N:4]/[C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[F:1])\[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 6101p-Toluenesulfonic acidHCID 95842-FluoroanilineHCID 24083Sulfuric acid magnesium salt (1:1)

Product 1

HCID 178505640HCID 178505640, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Dissolved 2-fluoroaniline (2.0 mL, 20.8 mmol, 1.05 eq) in 40 mL of anhydrous ether. Added Magnesium Sulfate (7146 mg, 59.3 mmol, 4 eq), 7 g of powdered mol sieves, and benzaldehyde (2.0 mL, 19.8 mmol). To this mixture was added pTsOH (18.8 mg, 98.9 μmol, 0.005 eq) and heated to reflux overnight. The reaction was cooled, filtered and concentrated to yield (E)-N-benzylidene-2-fluorobenzenamine. 1H NMR (400 MHz, CDCl3) δ ppm 8.55 (s, 1H), 7.95 (m, 2H), 7.52 (m, 5H), 7.18 (m, 4H).

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. temperatureThe reaction was cooled
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-82af78880ae349e2bd73c4fdc51aa674
Source dataset
uspto-grants-2014_12
Patent number
US08901135B2

Reaction notes

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