Water → N-[(3,4-Dichloro-phenylcarbamoyl)-methyl]-N-isobutyl-4-methoxy-benzamide

HRID 732966Notes

Reaction equation

HRID 732966 reaction equation
Br.[Cl:2][C:3]1[CH:4]=[C:5]([NH:10][C:11](=[O:18])[CH2:12][NH:13][CH2:14][CH:15]([CH3:17])[CH3:16])[CH:6]=[CH:7][C:8]=1[Cl:9].[CH3:19][O:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1.O>C1COCC1.C(N(CC)CC)C>[Cl:2][C:3]1[CH:4]=[C:5]([NH:10][C:11]([CH2:12][N:13]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:25](=[O:26])[C:24]2[CH:28]=[CH:29][C:21]([O:20][CH3:19])=[CH:22][CH:23]=2)=[O:18])[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

6

Reactant 3

HCID 962WaterHCID 7477p-Anisoyl chlorideHCID 68872127N-(3,4-Dichloro-phenyl)-2-isobutylamino-acetamide hydrobromide

Product 1

HCID 68875382N-[(3,4-Dichloro-phenylcarbamoyl)-methyl]-N-isobutyl-4-methoxy-benzamideYield 75.4%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of N-(3,4-dichloro-phenyl)-2-isobutylamino-acetamide hydrobromide (0.090 g) in THF were slowly added a solution of triethylamine (0.064 mg) in THF (5 mL) and a solution of 4-methoxybenzoyl chloride (47 mg) in THF (5 mL) and the reaction mixture was stirred at room temperature for 24 hours. Then water was added to the reaction mixture and the precipitate was isolated by filtration and then purified by column chromatography to yield the title compound (78 mg). MS (m/e): 409.2 (M−H, 100%).

Workup

  1. customthe precipitate was isolated by filtration
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-55ac440d737d488dba80cd9277d72060
Source dataset
uspto-grants-2009_09
Patent number
US07589089B2

Reaction notes

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