Pyridine → N-(4-bromo-3-chloro-phenyl)-3-chloro-propionamide

HRID 1774832Notes

Reaction equation

HRID 1774832 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[Cl:9].N1C=CC=CC=1.[Cl:16][CH2:17][CH2:18][C:19](Cl)=[O:20]>ClCCCl>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:19](=[O:20])[CH2:18][CH2:17][Cl:16])=[CH:4][C:3]=1[Cl:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 693643-Chloropropionyl chlorideHCID 888884-Bromo-3-chloroaniline

Product 1

HCID 86679184N-(4-bromo-3-chloro-phenyl)-3-chloro-propionamideYield 95%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 4-bromo-3-chloroaniline (6.0 g, 29.1 mmol) and pyridine (3.45 g, 43.6 mmol) in 1,2-dichloroethane (50 mL) was added 3-chloropropionyl chloride (5.53 g, 43.6 mmol) dropwise at 15° C. After stirring for 2 hours at room temperature, the mixture was washed with water and then hydrochloric acid (2 N, aqueous). The organic layer was dried over anhydrous sodium sulfate. After filtration, the solvent was removed under reduced pressure. The product N-(4-bromo-3-chloro-phenyl)-3-chloro-propionamide (8.20 g, yield: 95%) was obtained as an oil. MS: 298.0 (M+H+)+.

Workup

  1. washthe mixture was washed with water
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationAfter filtration
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-606ec1cb5b4540d6a24bf7050b190b74
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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