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

HRID 530339Notes

Reaction equation

HRID 530339 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) drop wise at 15° C. After stirring for 2 hr at room temperature, the mixture was washed with water and then 2 N aq. hydrochloric acid. The organic layer was dried over anhy. Na2SO4, and after filtration, the solvent was removed under reduced pressure. The product N-(4-bromo-3-chloro-phenyl)-3-chloro-propionamide (8.20 g, 95% yield) was obtained as oil. MS: 298.0 (M+H)+.

Workup

  1. washthe mixture was washed with water
  2. customThe organic layer was dried over anhy
  3. filtrationNa2SO4, and after filtration
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d7ea29047d4e472e879ba574c93f92e8
Source dataset
uspto-grants-2016_05
Patent number
US09353081B2

Reaction notes

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