Ethyl 4-chloroacetoacetate → Ethyl 2-cyclohexyl-4-thiazoleacetate

HRID 4400

Reaktionsgleichung

Reaktionsgleichung von HRID 4400
[CH:1]1([C:7](=[S:9])[NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH2:11][C:12](=O)[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]>C(O)C>[CH:1]1([C:7]2[S:9][CH:11]=[C:12]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 69484Ethyl 4-chloroacetoacetateHCID 12336049Cyclohexanecarbothioamide

Produkt 1

HCID 15026349Ethyl 2-cyclohexyl-4-thiazoleacetateAusbeute 71,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of cyclohexanethiocarboxamide (5.0 g), ethyl 4-chloroacetoacetate (5.74 g), ethanol (50 ml) was heated under reflux for 1 hour. After dilution with water, mixture was extracted with ethyl acetate. The extract was washed with aqueous sodium bicarbonate solution and water, dried (MgSO4), and concentrated. The residue was purified by chromatography on silica gel with ethyl acetate-hexane (1:4) to yield ethyl 2-cyclohexyl-4-thiazoleacetate as an oil (6.3 g, 70.9%). IR (Neat): 1735, 1255 cm-1. NMR (CDCl3)δ: 1.28 (3H, t, J=7 Hz), 1.2-2.3 (10H, m), 2.97 (1H, m), 3.77 (2H, s), 4.17 (2H, q, J=7 Hz), 7.0 (1H, s).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. extractionAfter dilution with water, mixture was extracted with ethyl acetate
  4. washThe extract was washed with aqueous sodium bicarbonate solution and water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel with ethyl acetate-hexane (1:4)

Quellen und Nachweise

ORD-Eintrag
ord-d744f03ba5db41d1bd7902f811b93a8d
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04725610

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