Acetanilide, 4'-chloro-2,2,2-trifluoro- → (4-Chlorophenyl) (2,2,2-trifluoroethyl)amine

HRID 897212Notes

Reaction equation

HRID 897212 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=O)[C:10]([F:13])([F:12])[F:11])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH2:9][C:10]([F:11])([F:12])[F:13])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 9830Acetanilide, 4'-chloro-2,2,2-trifluoro-HCID 21226445Aluminium lithium hydride

Product 1

HCID 10420625(4-Chlorophenyl) (2,2,2-trifluoroethyl)amineYield 87.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(4-Chlorophenyl)-trifluoroacetamide (2.22 g, 10 mmol) was dissolved in THF (100 mL) and treated with powdered lithium aluminum hydride (0.57 g, 15 mmol) under argon. The mixture was heated with stirring to reflux for 12 hours at which point both TLC and LC/MS analysis indicated the reaction was complete. The suspension was cooled in an ice bath prior to quenching with saturated aqueous sodium sulfate solution. The solution was dried with excess sodium sulfate and concentrated under reduced pressure to give 1.84 g of a viscous oil which was used without further purification. 1H NMR (300 MHz, CDCl3) δ ppm 3.70 (2H, dt, J=8.96, 15.81 Hz), 3.91 (1H, br s), 6.58 (2H, m), 7.13 (2H, m).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 12 hours at which point both TLC and LC/MS analysis
  3. temperatureThe suspension was cooled in an ice bath
  4. customto quenching with saturated aqueous sodium sulfate solution
  5. dry with materialThe solution was dried with excess sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6b7dbf09f7784ab5b6978d47a15be557
Source dataset
uspto-grants-2005_07
Patent number
US06921821B2

Reaction notes

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