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

HRID 1816589Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1816589
[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]

Komponenten

8

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 14798Sodium HydroxideLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-0ff6fa14399e4dd59211609cf54914cf
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06884821B1

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