Pyridine → 2,4-dichloro-N-[(2-methoxyphenyl)methyl]benzamide

HRID 1816589Notes

Reaction equation

HRID 1816589 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH3:12][O:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][NH2:17].N1C=CC=CC=1>CN(C)C=O.C(OCC)(=O)C.[Cl-].[NH4+].[OH-].[Na+]>[CH3:12][O:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][NH:17][C:4](=[O:5])[C:3]1[CH:7]=[CH:8][C:9]([Cl:11])=[CH:10][C:2]=1[Cl:1]

Participants

8

Reactant 3

HCID 1049PyridineHCID 666452,4-Dichlorobenzoyl chlorideHCID 812922-Methoxybenzylamine

Product 1

HCID 7960612,4-dichloro-N-[(2-methoxyphenyl)methyl]benzamide

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

45 mL 2,4-dichlorobenzoyl chloride was added dropwise over 1.5 hours into a solution of 50 ml 2-methoxybenzylamine and 123 ml pyridine in N,N-dimethylformamide (400 mL) at 5 to 10° C., followed by stirring at room temperature for 16 hours. The reaction solution was diluted with ethyl acetate, saturated aqueous ammonium chloride solution and 1N aqueous sodium hydroxide solution. The organic layer was washed with 1N aqueous sodium hydroxide solution, 1 N hydrochloric acid (×2), saturated aqueous ammonium chloride solution (×2) and brine, dried over anhydrous sodium sulfate and concentrated. The residue was suspended in diisopropyl ether (300 mL) and diethyl ether (500 mL). The solid was collected by filtration and washed with diethyl ether, to give 81.1 g of N1-(2-methoxybenzyl)-2,4-dichlorobenzamide as a pale yellow solid.

Workup

  1. washThe organic layer was washed with 1N aqueous sodium hydroxide solution, 1 N hydrochloric acid (×2), saturated aqueous ammonium chloride solution (×2) and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. filtrationThe solid was collected by filtration
  5. washwashed with diethyl ether

Sources & evidence

ORD record
ord-0ff6fa14399e4dd59211609cf54914cf
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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