Water → HCID 68849591, Verbindung

HRID 29226Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 29226
[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-:25]#[N:26].[K+].O>CN(C)C=O>[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][C:25]#[N:26])=[O:8]

Komponenten

5

Edukt 3

HCID 962WaterHCID 9032Potassium CyanideHCID 68849646HCID 68849646, Verbindung

Produkt 1

HCID 68849591HCID 68849591, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

A stirred solution of 2-(3,5-dichlorophenoxy)-N-(1-chloro-6-methylhept-4-yn-6-yl) butyramide (3.91) in dry N,N-dimethylformamide (35 ml) containing potassium cyanide (0.78 g) was heated to 95° C. for 6 hours, cooled to ambient temperature then stored for 18 hours. The mixture was poured into water, extracted with diethyl ether (three times) and the extracts were combined, washed with water (three times), dried over magnesium sulphate then evaporated under reduced pressure to give the required product as a yellow oil, 3.42 g. A portion of this material was fractionated by chromatography (silica; hexane/ethyl acetate 3:1 by volume) to give a pure sample of 2-(3,5-dichlorophenoxy)-N-(1-cyano-6-methylhept-4-yn-6-yl) butyramide as a yellow gum, 1H NMR (CDCl3) δ: 0.98-1.02(3H, t); 1.58(3H, s); 1.60(3H, s); 1.82-1.88(2H, m); 1.92-1.98(2H, m); 2.36-2.40(2H, t); 2.48-2.56(2H, m); 4.38-4.42(1H, t); 6.26(1H, s); 6.84(2H, s); 7.04(1H, s).

Aufarbeitung

  1. temperaturecooled to ambient temperature
  2. extractionextracted with diethyl ether (three times)
  3. washwashed with water (three times)
  4. dry with materialdried over magnesium sulphate
  5. customthen evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-83b3e87ca2384868ba75e3546211545d
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07420090B2

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