Selectfluor → HCID 68805719, compound

HRID 1270750Notes

Reaction equation

HRID 1270750 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[NH:5][C:6]1[C:15]([Cl:16])=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1)[CH3:2].[B-](F)(F)(F)[F:19].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:17])[NH:5][C:6]1[C:15]([Cl:16])=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]=1[F:19])[CH3:2]

Participants

4

Reactant 2

HCID 2724933SelectfluorHCID 13463001HCID 13463001, compound

Product 1

HCID 68805719HCID 68805719, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2.50 g (10 mmol) of N-(3-chloro-2-naphthyl)carbamic acid ethyl ester and 7.1 g of Selectfluor® (20 mmol) in 30 mL of CH2CN is heated to reflux under an atmosphere of nitrogen for 16 hours. After cooling to room temperature, the solids are filtered and the solvent is evaporated to give a residue that is diluted with 200 mL of EtOAc. The mixture is washed 3 times with 50 mL of H2O, once with 50 mL of saturated brine and dried over MgSO4. Evaporation of the solvents gives a residue that is purified by flash chromatography on silica gel (100% CH2Cl2) to give N-(1-fluoro-3-chloro-2-naphthyl)carbamic acid ethyl ester.

Workup

  1. temperatureis heated
  2. temperatureto reflux under an atmosphere of nitrogen for 16 hours
  3. filtrationthe solids are filtered
  4. customthe solvent is evaporated
  5. customto give a residue that
  6. washThe mixture is washed 3 times with 50 mL of H2O
  7. dry with materialonce with 50 mL of saturated brine and dried over MgSO4
  8. customEvaporation of the solvents
  9. customgives a residue that
  10. customis purified by flash chromatography on silica gel (100% CH2Cl2)

Sources & evidence

ORD record
ord-2c9892dba3f444ba9dd9b611695d80a0
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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