2-Chloro-4-hydroxybenzonitrile → 3-(3-Chloro-4-cyanophenoxy)-2-hydroxy-2-methyl-N-(2-methyl-4-nitrophenyl)propionamide

HRID 133769

Reaktionsgleichung

Reaktionsgleichung von HRID 133769
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:11][C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1[NH:21][C:22]([C:24]1([CH3:27])[CH2:26][O:25]1)=[O:23]>>[Cl:1][C:2]1[CH:9]=[C:8]([CH:7]=[CH:6][C:3]=1[C:4]#[N:5])[O:10][CH2:27][C:24]([OH:25])([CH3:26])[C:22]([NH:21][C:13]1[CH:14]=[CH:15][C:16]([N+:18]([O-:20])=[O:19])=[CH:17][C:12]=1[CH3:11])=[O:23]

Komponenten

3

Edukt 2

HCID 5927972-Chloro-4-hydroxybenzonitrileHCID 714200002-Methyl-N-(2-methyl-4-nitrophenyl)oxirane-2-carboxamide

Produkt 1

HCID 675255853-(3-Chloro-4-cyanophenoxy)-2-hydroxy-2-methyl-N-(2-methyl-4-nitrophenyl)propionamide

Versuchsvorschrift

3-(3-Chloro-4-cyanophenoxy)-2-hydroxy-2-methyl-N-(2-methyl-4-nitrophenyl)propionamide was prepared as described in Example 64c starting from 2-chloro-4-hydroxybenzonitrile and 2-methyloxirane-2-carboxylic acid (2-methyl-4-nitrophenyl)amide. The crude product was purified by flash chromatography (dichloromethane-1.3% methanol). 1H NMR (400 MHz, DMSO-d6): 1.46 (3H, s), 2.37 (3H, s), 4.15 (1H, d, J=10.1 Hz), 4.39 (1H, d, J=10.1 Hz), 6.51 (1H, s), 7.10 (1H, dd, J=8.8 Hz, J=2.4 Hz), 7.37 (1H, d, J=2.4 Hz), 7.86 (1H, d, J=8.8 Hz), 8.05-8.12 (2H, m), 8.18 (1H, d, J=2.3 Hz), 9.56 (1H, s).

Aufarbeitung

  1. customThe crude product was purified by flash chromatography (dichloromethane-1.3% methanol)

Quellen und Nachweise

ORD-Eintrag
ord-a851fd2e752749b5a9ae150f7f8c48ac
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390923B2

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