Aniline → N-(3,4-Dichloro-phenyl)-2-phenylamino-acetamide

HRID 732962Notes

Reaction equation

HRID 732962 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([Cl:13])[CH:7]=1)=[O:4].[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(C(C)C)C(C)C)C>C1COCC1>[Cl:13][C:8]1[CH:7]=[C:6]([NH:5][C:3](=[O:4])[CH2:2][NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:11]=[CH:10][C:9]=1[Cl:12]

Participants

5

Reactant 3

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 34147142-bromo-N-(3,4-dichlorophenyl)acetamide

Product 1

HCID 4013057N-(3,4-Dichloro-phenyl)-2-phenylamino-acetamideYield 1,000.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2-bromo-N-(3,4-dichloro-phenyl)-acetamide (2 g) in THF (80 mL) was added aniline (41 mg) and N-ethyldiisopropylamine and the reaction mixture was stirred over night at reflux. The precipitated salt was then filtered off and the filtrate was then concentrated in vacuo. The residue was then purified by column chromatography to give the title compound as a light brown solid (1.3 g, mp=110-112° C.).

Workup

  1. temperatureat reflux
  2. filtrationThe precipitated salt was then filtered off
  3. concentrationthe filtrate was then concentrated in vacuo
  4. customThe residue was then purified by column chromatography

Sources & evidence

ORD record
ord-4fb9c061612d47e7be6cf8c1001922d4
Source dataset
uspto-grants-2009_09
Patent number
US07589089B2

Reaction notes

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