1H-1,2,4-Triazole → HCID 68846595, Verbindung

HRID 29225Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 29225
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[C:22]([Cl:24])[CH:23]=1)[O:5][CH:6]([CH2:19][CH3:20])[C:7]([NH:9][C:10]([CH3:18])([CH3:17])[C:11]#[C:12][CH2:13][CH2:14][CH2:15]Cl)=[O:8].C(=O)([O-])[O-].[K+].[K+].[NH:31]1[CH:35]=[N:34][CH:33]=[N:32]1.CCCCCC.C(OCC)(=O)C>CN(C)C=O.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[C:22]([Cl:24])[CH:23]=1)[O:5][CH:6]([CH2:19][CH3:20])[C:7]([NH:9][C:10]([CH3:18])([CH3:17])[C:11]#[C:12][CH2:13][CH2:14][CH2:15][N:31]1[CH:35]=[N:34][CH:33]=[N:32]1)=[O:8]

Komponenten

8

Edukt 4

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 21226206Ethyl acetate hexaneHCID 68849646HCID 68849646, Verbindung

Produkt 1

HCID 68846595HCID 68846595, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a stirred solution of 2-(3,5-dichlorophenoxy)-N-(1-chloro-6-methylhept-4-yn-6-yl) butyramide (0.59 g) in dry N,N-dimethylformamide (10 ml) containing anhydrous potassium carbonate (0.28 g) was added 1,2,4-triazole (0.10 g). The mixture was heated to 90° C. for 2.75 hours, cooled to ambient temperature, diluted with water and extracted with ethyl acetate (three times). The extracts were combined, washed with brine, dried over magnesium sulphate then evaporated under reduced pressure to give a yellow oil. The oil was fractionated by chromatography (silica; hexane/ethyl acetate, 2:1 by volume followed by ethyl acetate) to give the required product as a colourless oil, 0.16 g, 1H NMR (CDCl3) δ: 1.00-1.06(3H, t); 1.60(3H, s); 1.62(3H, s); 1.92-2.14(6H, m); 4.38-4.44(3H, m); 6.26(1H, s); 6.84(2H, s); 7.04(1H, s); 7.96(1H, s); 8.32(1H, s).

Aufarbeitung

  1. temperaturecooled to ambient temperature
  2. extractionextracted with ethyl acetate (three times)
  3. washwashed with brine
  4. dry with materialdried over magnesium sulphate
  5. customthen evaporated under reduced pressure
  6. customto give a yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-8f1f3b306b914e7fa27b6e94b11fb820
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07420090B2

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