Thionyl Chloride → HCID 21890740, Verbindung

HRID 721594Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 721594
S(Cl)(Cl)=O.O(C(CC)C(O)=O)C1C=CC=CC=1.O(C(CC)C(Cl)=O)C1C=CC=CC=1.[O:31]([CH:38]([CH2:44][CH3:45])[C:39]([N:41]=[C:42]=[S:43])=[O:40])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[Cl:46][C:47]1[CH:48]=[C:49]([CH:51]=[CH:52][C:53]=1[O:54][C:55]1[C:64]2[C:59](=[CH:60][C:61]([O:67][CH3:68])=[C:62]([O:65][CH3:66])[CH:63]=2)[N:58]=[CH:57][CH:56]=1)[NH2:50]>C(O)C.C1(C)C=CC=CC=1>[Cl:46][C:47]1[CH:48]=[C:49]([NH:50][C:42]([NH:41][C:39](=[O:40])[CH:38]([O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:44][CH3:45])=[S:43])[CH:51]=[CH:52][C:53]=1[O:54][C:55]1[C:64]2[C:59](=[CH:60][C:61]([O:67][CH3:68])=[C:62]([O:65][CH3:66])[CH:63]=2)[N:58]=[CH:57][CH:56]=1

Komponenten

8

Edukt 5

HCID 24386Thionyl ChlorideHCID 579872-Phenoxybutanoic acidHCID 30848382-Phenoxybutanoyl chlorideHCID 117390273-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]anilineHCID 21891125HCID 21891125, Verbindung

Produkt 1

HCID 21890740HCID 21890740, VerbindungAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Toluene (20 ml) and thionyl chloride (1 ml) were added to commercially available 2-phenoxybutanoic acid (80 mg), and the mixture was heated at 100° C. for one hr. The solvent was removed by distillation, and 2-phenoxybutanoyl isothiocyanate was prepared using the resultant 2-phenoxybutanoyl chloride as a starting compound according to the description of the literature. 2-Phenoxybutanoyl isothiocyanate thus obatined was dissolved in ethanol (1 ml) to prepare a solution. 3-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]aniline (50 mg), toluene (5 ml), and ethanol (1 ml) were added to the solution, and the mixture was stirred at room temperature for 16 hr. The reaction solution was concentrated, and the residue was purified by chromatography on silica gel using chloroform/acetone for development to give the title compound (25 mg, yield 27%).

Aufarbeitung

  1. customThe solvent was removed by distillation, and 2-phenoxybutanoyl isothiocyanate
  2. customwas prepared
  3. customto prepare a solution
  4. concentrationThe reaction solution was concentrated
  5. customthe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-119b117dbd754e4f90a9320236093da7
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07135466B2

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