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Ethyl Acetoacetate → ethyl 6,7-dihydro-4-methyl-2-(4-chlorphenyl)-4H-pyrano[4,3-d]thiazole-4-acetate

HRID 258580
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Reaktionsgleichung

Reaktionsgleichung von HRID 258580
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[C:11]([CH2:13][CH2:14][OH:15])[N:12]=2)=[CH:4][CH:3]=1.[C:16]([O:22][CH2:23][CH3:24])(=[O:21])[CH2:17][C:18]([CH3:20])=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:20][C:18]1([CH2:17][C:16]([O:22][CH2:23][CH3:24])=[O:21])[C:10]2[S:9][C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)=[N:12][C:11]=2[CH2:13][CH2:14][O:15]1
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Komponenten

5

Edukt 3

HCID 8868Ethyl AcetoacetateHCID 521998p-Toluenesulfonic acid monohydrateHCID 6105314-Thiazoleethanol, 2-(4-chlorophenyl)-

Produkt 1

HCID 54049665ethyl 6,7-dihydro-4-methyl-2-(4-chlorphenyl)-4H-pyrano[4,3-d]thiazole-4-acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of the starting material of formula II, 2-(4-chlorophenyl)-4-(β-hydroxyethyl)thiazole (24.0 g, 0.1 mole, described in Example 1), ethyl acetoacetate (19.5 g, 0.15 mole) and p-toluenesulfonic acid hydrate (38.0 g, 0.2 mole) in toluene (1000 ml) is heated at reflux temperature, with water separation, for 20 hr. The mixture is evaporated under reduced pressure and the residue is triturated with petroleum ether. The residue is dissolved in a mixture of aqueous sodium bicarbonate solution and ether. The organic solution is separated, washed with saturated sodium chloride solution, dried over sodium sulfate and evaporated under reduced pressure to give ethyl 6,7-dihydro-4-methyl-2-(4-chlorphenyl)-4H-pyrano[4,3-d]thiazole-4-acetate (IV, R1 = Cl, R2 = CH3, A= COOCH2CH3 and n= 1).

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux temperature
  3. customwith water separation
  4. customThe mixture is evaporated under reduced pressure
  5. customthe residue is triturated with petroleum ether
  6. dissolutionThe residue is dissolved in a mixture of aqueous sodium bicarbonate solution and ether
  7. customThe organic solution is separated
  8. washwashed with saturated sodium chloride solution
  9. dry with materialdried over sodium sulfate
  10. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ff229ec221fa46848b65072111052928
Quelldatensatz
uspto-grants-1977_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04033977

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