Isobutylamine → N-(3,4-Dichloro-phenyl)-2-isobutylamino-acetamide hydrobromide

HRID 732965Notes

Reaction equation

HRID 732965 reaction equation
[Br:1][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].[CH2:14]([NH2:18])[CH:15]([CH3:17])[CH3:16]>ClCCl>[BrH:1].[Cl:13][C:8]1[CH:7]=[C:6]([NH:5][C:3](=[O:4])[CH2:2][NH:18][CH2:14][CH:15]([CH3:17])[CH3:16])[CH:11]=[CH:10][C:9]=1[Cl:12]

Participants

4

Reactant 2

HCID 6558IsobutylamineHCID 34147142-bromo-N-(3,4-dichlorophenyl)acetamide

Product 1

HCID 68872127N-(3,4-Dichloro-phenyl)-2-isobutylamino-acetamide hydrobromideYield 79.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-bromo-N-(3,4-dichloro-phenyl)-acetamide (0.1 g) in dichloromethane (80 mL) at 0° C. was slowly added of isobutylamine (52 mg) in dichloromethane. The reaction mixture was allowed to warm up to room temperature and then stirred for another 24 hours. Then the salt was filtered off and the filtrate was concentrated in vacuo. The residue was then purified by column chromatography to yield the title compound as a white solid (0.1 g). MS (m/e): 357.1 (M+H+).

Workup

  1. filtrationThen the salt was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was then purified by column chromatography

Sources & evidence

ORD record
ord-995b53747f004df09c82f0f9f9aff058
Source dataset
uspto-grants-2009_09
Patent number
US07589089B2

Reaction notes

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