Triethylamine → 2-Ethyl-4-(4-methoxyphenyl)-5-(3-pyridyl)-1,3-thiazole

HRID 65030Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 65030
[C:1]([NH2:5])(=[S:4])[CH2:2][CH3:3].Br[CH:7]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)=O.C(N(CC)CC)C>C(#N)C>[CH2:2]([C:1]1[S:4][C:7]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[C:8]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)[N:5]=1)[CH3:3]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 2760628PropanethioamideHCID 114633372-Bromo-1-(4-methoxyphenyl)-2-(3-pyridyl)ethanone

Produkt 1

HCID 135188862-Ethyl-4-(4-methoxyphenyl)-5-(3-pyridyl)-1,3-thiazoleAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

In 40 ml of acetonitrile was dissolved 493 mg of thiopropionic acid amide. In the solution was suspended 2.15 g of 2-bromo-1-(4-methoxyphenyl)-2-(3-pyridyl)ethanone. To the suspension was added dropwise slowly 0.78 ml of triethylamine while stirring. The mixture was stirred for 3 hours at a refluxing temperature, then the solvent was evaporated off. To the residue was added a saturated aqueous solution of sodium hydrogen carbonate. The mixture was subjected to extraction with ethyl acetate. The extract was dried, then the solvent was evaporated off. The residue was recrystallised from ethyl acetate-isopropyl ether to yield 1.38 g (91%) of 2-ethyl-4-(4-methoxyphenyl)-5-(3-pyridyl)-1,3-thiazole, m.p. 59°-60° C.

Aufarbeitung

  1. stirringThe mixture was stirred for 3 hours at a refluxing temperature
  2. customthe solvent was evaporated off
  3. additionTo the residue was added a saturated aqueous solution of sodium hydrogen carbonate
  4. extractionThe mixture was subjected to extraction with ethyl acetate
  5. customThe extract was dried
  6. customthe solvent was evaporated off
  7. customThe residue was recrystallised from ethyl acetate-isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-9d3e44a81a0c491c88d9be5f26fc44e9
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04612321

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