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

HRID 1816589노트

반응식

HRID 1816589 반응식
[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]

참가 물질

8

반응물 3

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

생성물 1

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

시약·촉매·용매 4

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매HCID 14798Sodium Hydroxide용매HCID 25517Ammonium Chloride용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0ff6fa14399e4dd59211609cf54914cf
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06884821B1

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