Dimethylformamide → 2-Phenoxyacetamide

HRID 1820007Notes

Reaction equation

HRID 1820007 reaction equation
CN(C=O)C.[OH:6][C:7]1[CH:12]=[CH:11][C:10](C(=O)C)=[CH:9][CH:8]=1.Br[CH2:17][C:18]([NH:20]C1C=CC(Br)=CC=1)=[O:19].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[O:6]([CH2:17][C:18]([NH2:20])=[O:19])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 74694'-HydroxyacetophenoneHCID 11430Potassium CarbonateHCID 2255262-Bromo-n-(4-bromophenyl)acetamide

Product 1

HCID 693142-PhenoxyacetamideYield 223.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

DMF (20 ml) was added to 1-(4-hydroxyphenyl)ethanone (1.81 g, 13.3 mmol), 2-bromo-N-(4-bromophenyl)acetamide (3.00 g, 10.2 mmol), and potassium carbonate (4.25 g, 30.7 mmol), and the mixture was stirred at room temperature for 16 hrs. The reaction mixture was diluted with ethyl acetate, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by alumina column chromatography (developing solvent; ethyl acetate), and powderized with ethyl acetate-diisopropyl ether (1:5) to give a phenoxyacetamide derivative (3.44 g). The title compound was obtained by similar operations as in Reference Example 20, Reference Example 21, Example 10 and Example 6 and using this compound.

Workup

  1. washwashed with saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe obtained residue was purified by alumina column chromatography (developing solvent; ethyl acetate)

Sources & evidence

ORD record
ord-3af50f1152b245d490ce5f0b5dd7807e
Source dataset
uspto-grants-2009_10
Patent number
US07601868B2

Reaction notes

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