3,5-Dichloroaniline → HCID 19978192, compound

HRID 1449504Notes

Reaction equation

HRID 1449504 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Cl:9])[CH:8]=1)[NH2:5].Br[CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]>CN(C)C=O>[CH2:16]([O:15][C:13]([CH2:12][CH2:11][NH:5][C:4]1[CH:3]=[C:2]([Cl:1])[CH:8]=[C:7]([Cl:9])[CH:6]=1)=[O:14])[CH3:17]

Participants

4

Reactant 2

HCID 122813,5-DichloroanilineHCID 68320Ethyl 3-bromopropionate

Product 1

HCID 19978192HCID 19978192, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 20 ml of dimethylformamide was dissolved 5.0 g of 3,5-dichloroaniline. To the solution was added 6.16 g of ethyl 3-bromopropionate, followed by heating under reflux for 6 hours. The reaction mixture was concentrated and the concentrate was extracted with ethyl acetate. The extract was washed with saturated sodium hydrogencarbonate aqueous solution and saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was subjected-to silica gel column chromatography (eluent: chloroform:hexane=1:1) to yield 3.98 g of the titled compound as a white crystal.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 6 hours
  3. concentrationThe reaction mixture was concentrated
  4. extractionthe concentrate was extracted with ethyl acetate
  5. washThe extract was washed with saturated sodium hydrogencarbonate aqueous solution and saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f34c84f955864d789d016137a0f23747
Source dataset
uspto-grants-1997_02
Patent number
US05599813

Reaction notes

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