Benzaldehyde → HCID 178505640, compound

HRID 216813Notes

Reaction equation

HRID 216813 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 μl, 19.8 mmol). To this mixture was added pTsOH (18.8 mg, 98.9 jμmol, 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-c4dd0cd93cf446d79c0c4becb1b950e9
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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