Hydrochloric Acid → HCID 178418604, Verbindung

HRID 5263

Reaktionsgleichung

Reaktionsgleichung von HRID 5263
[CH2:1]1[C:6](=[O:7])[S:5][CH2:4][C:2]1=[O:3].C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC.[C:27](O)(=[O:45])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]/[CH:35]=[CH:36]\[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44].Cl>CN(C)C=O>[OH:3][C:2]1[CH2:4][S:5][C:6](=[O:7])[C:1]=1[C:27](=[O:45])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]/[CH:35]=[CH:36]\[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 445639Oleic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10214383Thiotetronic acid

Produkt 1

HCID 178418604HCID 178418604, VerbindungAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirring solution of 1.71 g (14.75 mmol) of thiotetronic acid in 10 mL of dimethylformamide is added 2.22 mL (17.2 mmol) of triethylamine and 592 mg (4.85 mmol) of 4-diemthylaminopyridine at 0° C. Next, 3.38 g (17.6 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 5.0 g (17.7 mmol) of oleic acid are added and the reaction mixture is stirred overnight at room temperature. The reaction is acidified with 1.0N HCl and extracted three times with diethyl ether. The combined organic layers are washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue is subjected to HPLC chromatography (2 inch Dynamax silica gel column, 25 mL/min) eluting with 100% ethyl acetate to give 1.85 g (33%) of 4-hydroxy-3-[(Z)-1-oxo-9-octadecenyl]-2(5H)-thiophenone as an oil.

Aufarbeitung

  1. extractionextracted three times with diethyl ether
  2. washThe combined organic layers are washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washeluting with 100% ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-56f204da68f24bf2af050b76d59dd02c
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05242945

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