p-Toluenesulfonic acid → Butyl-[1-(2-fluoro-4,6-bis-trifluoromethyl-phenyl)-methylidene]-amine

HRID 659214Notes

Reaction equation

HRID 659214 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([C:14]([F:17])([F:16])[F:15])[C:3]=1[CH:4]=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:29]([NH2:33])[CH2:30][CH2:31][CH3:32]>C1(C)C=CC=CC=1>[CH2:29]([N:33]=[CH:4][C:3]1[C:6]([C:14]([F:17])([F:16])[F:15])=[CH:7][C:8]([C:10]([F:13])([F:12])[F:11])=[CH:9][C:2]=1[F:1])[CH2:30][CH2:31][CH3:32]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8007ButylamineHCID 467374972-Fluoro-4,6-bis(trifluoromethyl)benzaldehyde

Product 1

HCID 58167770Butyl-[1-(2-fluoro-4,6-bis-trifluoromethyl-phenyl)-methylidene]-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Fluoro-4,6-bis(trifluoromethyl)benzaldehyde (10 g, 38 mmol) was dissolved in 30 mL toluene. p-Toluenesulfonic acid (140 mg, 0.74 mmol) and N-butylamine (2.94 g, 40 mmol) were added. The reaction mixture was refluxed overnight. The mixture was extracted with 2N sodium carbonate solution and ethyl acetate. The combined organic phases were dried on sodium sulfate, filtered and evaporated. The crude material, orange oil (12 g, >100%) was used without further purification.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. extractionThe mixture was extracted with 2N sodium carbonate solution and ethyl acetate
  3. customThe combined organic phases were dried on sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude material, orange oil (12 g, >100%) was used without further purification

Sources & evidence

ORD record
ord-c86120b2b6fc4b31ade3d2fc3f034463
Source dataset
uspto-grants-2011_12
Patent number
US08080541B2

Reaction notes

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