Triethylamine → 2-Propionylthioquinoline

HRID 1490346Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1490346
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:7]=1[SH:16].C(N(CC)CC)C>C(Cl)Cl>[C:1]([S:16][C:7]1[CH:8]=[CH:9][C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:6]=1)(=[O:4])[CH2:2][CH3:3]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 178418736HCID 178418736, Verbindung

Produkt 1

HCID 196989512-PropionylthioquinolineAusbeute 53,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

480 mg (1.2 equivalents) of propionyl chloride were added, whilst ice-cooling, to a solution of 1 g of 2-quinolinethiol and 0.83 ml (1.2 equivalents) of triethylamine in 20 ml of anhydrous methylene chloride, and the resulting mixture was stirred for 30 minutes. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting residue was mixed with ethyl acetate. This mixture was washed twice with a dilute aqueous solution of sodium hydrogencarbonate and was then washed with water. The organic layer was separated and dried over anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure. The residue was purified by flash chromatography through silica gel, using a 1:1 by volume mixture of cyclohexane and ethyl acetate as the eluent, to give 600 mg of the title compound having an Rf value of 0.4.

Aufarbeitung

  1. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  2. additionthe resulting residue was mixed with ethyl acetate
  3. washThis mixture was washed twice with a dilute aqueous solution of sodium hydrogencarbonate
  4. washwas then washed with water
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed by distillation under reduced pressure
  8. customThe residue was purified by flash chromatography through silica gel
  9. additionby volume mixture of cyclohexane and ethyl acetate as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-26e5d5b9ff174b05a24183212385c89d
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05681951

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