Potassium Carbonate → N-(5-chloro-2-oxiranylmethoxy-phenyl)-acetamide

HRID 584605Notes

Reaction equation

HRID 584605 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[CH:7]=1.C([O-])([O-])=O.[K+].[K+].[CH2:19]([CH:21]1[O:23][CH2:22]1)Br>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH2:19][CH:21]2[CH2:22][O:23]2)=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 952582-Acetylamino-4-chlorophenol

Product 1

HCID 22313737N-(5-chloro-2-oxiranylmethoxy-phenyl)-acetamideYield 66.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of N-(5-Chloro-2-hydroxy-phenyl)-acetamide (0.499 g, 2.68 mmol), K2CO3 (0.60 g, 4.35 mmol) and epibromohydrin (0.405 g, 2.95 mmol) in DMF (5 ml) was heated with stirring at 50° C. for 2 hours. The mixture was then partitioned between EtOAc and water 40+40 ml. The organic phase was washed twice with water and once with brine and finally concentrated in vacuo to give a crude product. The crude product was purified on silica (heptane:EtOAc, 1:1), to give 0.43 g (66%) of a white solid.

Workup

  1. customThe mixture was then partitioned between EtOAc and water 40+40 ml
  2. washThe organic phase was washed twice with water and once with brine
  3. concentrationfinally concentrated in vacuo
  4. customto give a crude product
  5. customThe crude product was purified on silica (heptane:EtOAc, 1:1)

Sources & evidence

ORD record
ord-d9901b4943d0433a962d8177360e52cf
Source dataset
uspto-grants-2005_08
Patent number
US06927222B2

Reaction notes

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