Water → Phenyl (2-fluoroethyl)carbamate

HRID 387880Notes

Reaction equation

HRID 387880 reaction equation
[F:1][CH2:2][CH2:3][NH2:4].N1C=CC=CC=1.Cl[C:12]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:13].O>CN(C)C=O.C(OCC)(=O)C>[F:1][CH2:2][CH2:3][NH:4][C:12](=[O:13])[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 99962-FluoroethylamineHCID 15891Phenyl chloroformate

Product 1

HCID 22936733Phenyl (2-fluoroethyl)carbamateYield 86.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

After dissolving 2-fluoroethylamine (0.5 g, 5.0321 mmol) in dimethylformamide (10 ml), pyridine (0.87 ml, 10.5674 mmol) was added at room temperature and the mixture was stirred. It was then cooled on ice, phenyl chloroformate (0.67 ml, 5.2837 mmol) was added dropwise, and after the dropwise addition the mixture was stirred at room temperature for 2.5 hours. Water was added to the reaction solution, extraction was performed with ethyl acetate, the extract was washed with saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain the title compound (0.797 g, 4.3509 mmol, 86.46%) as light yellow crystals.

Workup

  1. additionwas added at room temperature
  2. additionwas added dropwise
  3. additionafter the dropwise addition the mixture
  4. stirringwas stirred at room temperature for 2.5 hours
  5. washthe extract was washed with saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-219bf5e7ad3a45d0a0507ce1e1d5cd7a
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

Loading…