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

HRID 1816589ノート

反応式

HRID 1816589 の反応式
[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]

参加物

8

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒HCID 14798Sodium Hydroxide溶媒HCID 25517Ammonium Chloride溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0ff6fa14399e4dd59211609cf54914cf
出典データセット
uspto-grants-2005_04
特許番号
US06884821B1

反応ノート

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