Water → Methyl 4'-[(3-butyl-1,4-dihydro-4-thioxo-1-quinolinyl)-methyl](1,1'-biphenyl)-2-carboxylate

HRID 1602935Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1602935
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[CH2:23]([C:27]1[C:36](=O)[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]([CH2:38][C:39]2[CH:44]=[CH:43][C:42]([C:45]3[C:46]([C:51]([O:53][CH3:54])=[O:52])=[CH:47][CH:48]=[CH:49][CH:50]=3)=[CH:41][CH:40]=2)[CH:28]=1)[CH2:24][CH2:25][CH3:26].O.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH2:23]([C:27]1[C:36](=[S:10])[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]([CH2:38][C:39]2[CH:44]=[CH:43][C:42]([C:45]3[C:46]([C:51]([O:53][CH3:54])=[O:52])=[CH:47][CH:48]=[CH:49][CH:50]=3)=[CH:41][CH:40]=2)[CH:28]=1)[CH2:24][CH2:25][CH3:26]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 87949Lawesson's reagentHCID 19608515Methyl 4'-[(3-butyl-1,4-dihydro-4-oxo-1-quinolinyl)-methyl](1,1'-biphenyl)-2-carboxylate

Produkt 1

HCID 19608518Methyl 4'-[(3-butyl-1,4-dihydro-4-thioxo-1-quinolinyl)-methyl](1,1'-biphenyl)-2-carboxylateAusbeute 26.169,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

2.10 mg of Lawesson reagent were added to a solution of 400 mg of the product of Example 3 in 20 ml of toluene and the mixture was refluxed for 90 minutes. The mixture was poured into 100 ml of water and extraction was carried out with ethyl acetate. Th extracts were washed with water, dried, filtered and evaporated to dryness to obtain 0.6 g of the expected product which was chromatographed on silica (eluant: methylene chloride-acetone (98-2)) to collect 0.42 g of the desired product melting at 158° C.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 90 minutes
  2. washTh extracts were washed with water
  3. customdried
  4. filtrationfiltered
  5. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-f22d7c889e74403c910ba11a563cf17e
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05985894

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