4-Fluoro-3-(trifluoromethyl)phenol → 3-(4-Fluoro-3-trifluoromethylphenoxy)-2-hydroxy-2-methyl-N-(3-methyl-4-nitrophenyl)propionamide

HRID 133749

Reaktionsgleichung

Reaktionsgleichung von HRID 133749
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].[CH3:13][C:14]1[CH:15]=[C:16]([NH:23][C:24]([C:26]2([CH3:29])[CH2:28][O:27]2)=[O:25])[CH:17]=[CH:18][C:19]=1[N+:20]([O-:22])=[O:21]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:29][C:26]([OH:27])([CH3:28])[C:24]([NH:23][C:16]2[CH:17]=[CH:18][C:19]([N+:20]([O-:22])=[O:21])=[C:14]([CH3:13])[CH:15]=2)=[O:25])=[CH:4][C:3]=1[C:9]([F:10])([F:11])[F:12]

Komponenten

3

Edukt 2

HCID 6018544-Fluoro-3-(trifluoromethyl)phenolHCID 714200032-Methyl-N-(3-methyl-4-nitrophenyl)oxirane-2-carboxamide

Produkt 1

HCID 675266703-(4-Fluoro-3-trifluoromethylphenoxy)-2-hydroxy-2-methyl-N-(3-methyl-4-nitrophenyl)propionamide

Versuchsvorschrift

3-(4-Fluoro-3-trifluoromethylphenoxy)-2-hydroxy-2-methyl-N-(3-methyl-4-nitrophenyl)propionamide was prepared as described in Example 1 starting from 4-fluoro-3-(trifluoromethyl)phenol and 2-methyloxirane-2-carboxylic acid (3-methyl-4-nitrophenyl)amide. The crude product was purified by flash chromatography (dichloromethane-1% methanol). 1H NMR (400 MHz, DMSO-d6): 1.44 (3H, s), 2.53 (3H, s), 4.06 (1H, d, J=9.9 Hz), 4.32 (1H, d, J=9.9 Hz), 6.23 (1H, s), 7.24-7.31 (2H, m), 7.38-7.43 (1H, m), 7.87 (1H, dd, J=9.0 Hz, J=2.1 Hz), 7.91 (1H, d, J=2.0 Hz), 8.03 (1H, d, J=9.0 Hz), 10.14 (1H, s).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-52e64b4066d4464ba03414131d32cf32
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390923B2

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