Thionyl Chloride → N-{3-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-N'-(4-cyclohexylbenzoyl)thiourea

HRID 721900Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 721900
S(Cl)(Cl)=O.C1(C2C=CC(C(O)=O)=CC=2)CCCCC1.C1(C2C=CC(C(Cl)=O)=CC=2)CCCCC1.[Cl:35][C:36]1[CH:37]=[C:38]([CH:40]=[CH:41][C:42]=1[O:43][C:44]1[C:53]2[C:48](=[CH:49][C:50]([O:56][CH3:57])=[C:51]([O:54][CH3:55])[CH:52]=2)[N:47]=[CH:46][CH:45]=1)[NH2:39].[CH:58]1([C:64]2[CH:69]=[CH:68][C:67]([C:70]([N:72]=[C:73]=[S:74])=[O:71])=[CH:66][CH:65]=2)[CH2:63][CH2:62][CH2:61][CH2:60][CH2:59]1>C1(C)C=CC=CC=1.C(O)C>[Cl:35][C:36]1[CH:37]=[C:38]([NH:39][C:73]([NH:72][C:70](=[O:71])[C:67]2[CH:68]=[CH:69][C:64]([CH:58]3[CH2:59][CH2:60][CH2:61][CH2:62][CH2:63]3)=[CH:65][CH:66]=2)=[S:74])[CH:40]=[CH:41][C:42]=1[O:43][C:44]1[C:53]2[C:48](=[CH:49][C:50]([O:56][CH3:57])=[C:51]([O:54][CH3:55])[CH:52]=2)[N:47]=[CH:46][CH:45]=1

Komponenten

8

Edukt 5

HCID 24386Thionyl ChlorideHCID 883374-Cyclohexylbenzoic acidHCID 117390273-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]anilineHCID 218904044-Cyclohexyl-1-benzenecarbonyl isothiocyanateHCID 218908474-Cyclohexylbenzoyl chloride

Produkt 1

HCID 21890563N-{3-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-N'-(4-cyclohexylbenzoyl)thioureaAusbeute 54 %

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 4-cyclohexylbenzoic acid (80 mg), and the mixture was heated at 100° C. for one hr. The solvent was removed by distillation, and 4-cyclohexyl-1-benzenecarbonyl isothiocyanate was prepared using the resultant 4-cyclohexyl-1-benzenecarbonyl chloride as a starting compound according to the description of the literature. 3-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]aniline (50 mg) was dissolved in toluene (5 ml) and ethanol (1 ml) to prepare a solution. A solution of 4-cyclohexyl-1-benzenecarbonyl isothiocyanate in ethanol (1 ml) was then added to the solution, and the mixture was stirred at room temperature for 2 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 (47 mg, yield 54%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-113335b46c4641bd98dc3bf0a49ee572
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07135466B2

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