Ethanol → HCID 22009660, Verbindung

HRID 322326

Reaktionsgleichung

Reaktionsgleichung von HRID 322326
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[S:8])[NH2:7].[K].Cl[C:11]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=O.C(O)C>C(O)(=O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[S:8][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:11][N:7]=1

Komponenten

5

Edukt 3

HCID 702EthanolHCID 7372372-ThiophenecarbothioamideHCID 86756575HCID 86756575, Verbindung2×

Produkt 1

HCID 22009660HCID 22009660, VerbindungAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel2×

Versuchsvorschrift

Acetic acid (3.78 ml) was added to a stirred mixture of 2-thiophenecarbothioamide (3.15 g), ethyl chloroformylacetate potassium salt (6.23 g) and ethanol (60 ml). Afte refluxing for 4 h, ethyl chloroformylacetate potassium salt (4.15 g) and acetic acid (2.52 ml) were added, and then the refluxing was continued for further 20 h. The reaction mixture was concentrated, diluted with saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated to give an oil which was purified by silica gel column chromatography. From the fraction eluted with ethyl acetate-hexane (1:1, v/v) the crystals of ethyl 2-(2-thienyl)-5-thiazolecarboxylate (3.29 g, 63%) were obtained. Recrystallization from ethyl acetate-hexane gave colorless needles, mp 61-62° C.

Aufarbeitung

  1. temperatureAfte refluxing for 4 h
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with saturated aqueous sodium bicarbonate
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto give an oil which
  9. customwas purified by silica gel column chromatography
  10. washFrom the fraction eluted with ethyl acetate-hexane (1:1

Quellen und Nachweise

ORD-Eintrag
ord-1cdddae9b597462c85738ff34a12fc05
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211215B1

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