Hydrochloric Acid → 2,4-Dichloro-N-(2-chlorophenyl)benzamide

HRID 509567Notes

Reaction equation

HRID 509567 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[Cl:9][C:10]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:11]=1[C:12](Cl)=[O:13].C(N(CC)CC)C.Cl>ClCCl.C(OCC)(=O)C>[Cl:9][C:10]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:11]=1[C:12]([NH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[Cl:1])=[O:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 72402-ChloroanilineHCID 8471TriethylamineHCID 666452,4-Dichlorobenzoyl chloride

Product 1

HCID 3467412,4-Dichloro-N-(2-chlorophenyl)benzamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-chloroaniline (5.15 g, 40.37 mmol) in dichloromethane (50 mL) was added 2,4-dichlorobenzoyl chloride 1 (8.88 g, 42.39 mmol) and then triethylamine (6.1 mL, 44 mmol). The reaction mixture was stirred overnight at ambient temperature and ethyl acetate (150 mL) was added followed by 1N HCl (50 mL). The organic phase was washed with water and brine, dried, and concentrated under reduced pressure to yield a light yellow solid. 2,4-dichloro-N-(2-chlorophenyl)benzamide 2 was used for the next step without further purification. Yield: 11 g, 90%.

Workup

  1. washThe organic phase was washed with water and brine
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customto yield a light yellow solid
  5. custom2,4-dichloro-N-(2-chlorophenyl)benzamide 2 was used for the next step without further purification

Sources & evidence

ORD record
ord-9d0c971fbe644bcbb427f5a92bb8e723
Source dataset
uspto-grants-2015_08
Patent number
US09096587B2

Reaction notes

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