Thiobenzamide → Methyl 2-methyl2-[7-(2-phenyltiazole-4-yl)heptyloxy]propionate

HRID 857249Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 857249
[C:1]([NH2:9])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:11][C:12](=O)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]([CH3:27])([CH3:26])[C:22]([O:24][CH3:25])=[O:23]>C(OCC)(=O)C>[CH3:27][C:21]([O:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:12]1[N:9]=[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[S:8][CH:11]=1)([CH3:26])[C:22]([O:24][CH3:25])=[O:23]

Komponenten

4

Edukt 2

HCID 683563ThiobenzamideHCID 21866630Methyl 2-(9-chloro-8-oxononyloxy)-2-methylpropionate

Produkt 1

HCID 131725276Methyl 2-methyl2-[7-(2-phenyltiazole-4-yl)heptyloxy]propionateAusbeute 75,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 783 mg of thiobenzamide and 1.0 g methyl 2-(9-chloro-8-oxononyloxy)-2-methylpropionate were stirred for 2 hours at 120° C. The reaction solution was cooled and dissolved in ethyl acetate, washed by adding sodium hydrogencarbonate, washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane: ethyl acetate=9:1) to provide 963 mg of the objective compound as pale yellow oil.

Aufarbeitung

  1. temperatureThe reaction solution was cooled
  2. washwashed
  3. additionby adding sodium hydrogencarbonate
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (Wakogel® C-200, n-hexane: ethyl acetate=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-ee647066eea1453dbdb980314ac6d48f
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07144906B2

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