Water → 4-[(2-fluoroethyl)amino]furan-2(5H)-one

HRID 1037647Notes

Reaction equation

HRID 1037647 reaction equation
O.Cl.[F:3][CH2:4][CH2:5][NH2:6].[CH2:7]1[C:12](=[O:13])[O:11][CH2:10][C:8]1=O.C([O-])(=O)C.[Na+]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[F:3][CH2:4][CH2:5][NH:6][C:8]1[CH2:10][O:11][C:12](=[O:13])[CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 9995Ethanamine, 2-fluoro-, hydrochlorideHCID 517045Sodium AcetateHCID 521261Tetronic acid

Product 1

HCID 552864454-[(2-fluoroethyl)amino]furan-2(5H)-oneYield 42%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

On a water separator, 550 mg (4.97 mmol) of 2-fluoroethylamine hydrochloride, 547 mg (547 mmol) of tetronic acid, 408 mg (4.97 mmol) of sodium acetate and 9 mg (0.05 mmol) of 4-toluene sulphonic acid in 50 ml of toluene are heated under reflux for 5 hours. The reaction mixture is concentrated under reduced pressure and then taken up in ethyl acetate and washed with 1 N aqueous sodium hydroxide solution. The aqueous phase is extracted repeatedly with ethyl acetate and the combined organic phase is dried over sodium sulphate. Concentration of the organic phase under reduced pressure and purification of the residue by recrystallization from ethyl acetate/cyclohexane gives 300 mg (42% of theory) of 4-[(2-fluoroethyl)amino]furan-2(5H)-one.

Workup

  1. temperatureunder reflux for 5 hours
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. washwashed with 1 N aqueous sodium hydroxide solution
  4. extractionThe aqueous phase is extracted repeatedly with ethyl acetate
  5. dry with materialthe combined organic phase is dried over sodium sulphate
  6. customConcentration of the organic phase under reduced pressure and purification of the residue
  7. customby recrystallization from ethyl acetate/cyclohexane

Sources & evidence

ORD record
ord-a77b170b10cc4a3c91f238b33f0637fc
Source dataset
uspto-grants-2013_10
Patent number
US08546577B2

Reaction notes

Loading…