Water → Phenyl (2-fluoroethyl)carbamate

HRID 853402Notes

Reaction equation

HRID 853402 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 brine 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 brine
  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-6744e814724147009dc43a94edb0c7a8
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

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