Pyridine → N-(4-bromo-2-chlorophenyl)-3-chloropropanamide

HRID 1774841Notes

Reaction equation

HRID 1774841 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([Cl:9])[CH:3]=1.N1C=CC=CC=1.[Cl:16][CH2:17][CH2:18][C:19](Cl)=[O:20]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:19](=[O:20])[CH2:18][CH2:17][Cl:16])=[C:4]([Cl:9])[CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 693643-Chloropropionyl chlorideHCID 6101694-Bromo-2-chloroaniline

Product 1

HCID 43346898N-(4-bromo-2-chlorophenyl)-3-chloropropanamideYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-2-chloro-phenylamine (32 g, 0.15 mol) and pyridine (13.45 g, 0.17 mol) in DCM (200 mL) was added 3-chloropropionyl chloride (21.65 g, 0.17 mol) dropwise at 15° C. After stirring at room temperature for 1 hour, the mixture was washed with water and then hydrochloric acid (2 N, aqueous). The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to afford title compound (10.9 g, yield: 90%) as a white solid.

Workup

  1. washthe mixture was washed with water
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-376d4e64907a4af691c7f643a8dc1947
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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