Water → HCID 86584266, compound

HRID 1280375Notes

Reaction equation

HRID 1280375 reaction equation
[Cl:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])=[CH:6][C:5]([NH:16][C:17](=[O:19])[CH3:18])=[C:4]([F:20])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].O>CN(C)C=O>[C:17]([NH:16][C:5]1[C:4]([F:20])=[CH:3][C:2]([Cl:1])=[C:7]([CH:6]=1)[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])(=[O:19])[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 18759319N-[4-chloro-2-fluoro-5-(2-hydroxyphenoxy)phenyl]acetamide

Product 1

HCID 86584266HCID 86584266, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-[4-chloro-2-fluoro-5-(2-hydroxyphenoxy)phenyl]acetamide is dissolved in N,N-dimethylformamide, then, potassium carbonate is added and the mixture is stirred at room temperature. Then, ethyl bromoacetate is added at room temperature. The mixture is stirred under the same temperature, poured into water, extracted with ethyl acetate, the organic layer is washed with dilute hydrochloric acid, washed with water, dried over magnesium sulfate and concentrated, and the resulted crystal is washed with t-butyl methyl ether to obtain ethyl [2-(5-acetylamino-2-chloro-4-fluorophenoxy)phenoxy]acetate.

Workup

  1. stirringThe mixture is stirred under the same temperature
  2. extractionextracted with ethyl acetate
  3. washthe organic layer is washed with dilute hydrochloric acid
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. washthe resulted crystal is washed with t-butyl methyl ether

Sources & evidence

ORD record
ord-7a50392e1c354d5d97eef2491c544dc4
Source dataset
uspto-grants-2002_09
Patent number
US06451740B2

Reaction notes

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