Pyridine → HCID 86672139, compound

HRID 1842873Notes

Reaction equation

HRID 1842873 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH2:11][O:12][CH3:13])[NH2:5].N1C=CC=CC=1.Cl[C:21]([O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:22]>CC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([NH:5][C:21](=[O:22])[O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH2:11][O:12][CH3:13]

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 234981173-Fluoro-4-(2-methoxyethoxy)aniline

Product 1

HCID 86672139HCID 86672139, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 3-fluoro-4-(2-methoxyethoxy)aniline (2.0 g, 10.8 mmol, 1.0 eq) in acetone (50 mL) was added pyridine (2.5 mL, 32.4 mol, 3.0 eq.) and phenyl chloroformate (1.36 mL, 10.8 mmol, 1.0 eq.) at 0° C. and stirred at RT for 1 h. The solvent was evaporated, the residue diluted with EtOAc (50 mL), washed with water (100 mL), brine (20 mL) and evaporated again. The resulting residue was purified by column chromatography using EtOAc/PE (1:4) as eluent to yield phenyl 3-fluoro-4-(2-methoxyethoxy)phenylcarbamate (2.7 g, 76.8%) as a white solid (TLC system: EtOAc/PE (3:7), Rf: 0.5).

Workup

  1. customThe solvent was evaporated
  2. additionthe residue diluted with EtOAc (50 mL)
  3. washwashed with water (100 mL), brine (20 mL)
  4. customevaporated again
  5. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-73c24fb3d10441c3ad9d100ac3e2fe97
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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