3,5-Dimethylbenzoic acid → N-{3-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-N'-(3,5-dimethylbenzoyl)thiourea

HRID 721795

Reaktionsgleichung

Reaktionsgleichung von HRID 721795
S(Cl)(Cl)=O.CC1C=C(C=C(C)C=1)C(O)=O.CC1C=C(C(Cl)=O)C=C(C)C=1.[CH3:27][C:28]1[CH:29]=[C:30]([C:35]([N:37]=[C:38]=[S:39])=[O:36])[CH:31]=[C:32]([CH3:34])[CH:33]=1.[Cl:40][C:41]1[CH:42]=[C:43]([CH:45]=[CH:46][C:47]=1[O:48][C:49]1[C:58]2[C:53](=[CH:54][C:55]([O:61][CH3:62])=[C:56]([O:59][CH3:60])[CH:57]=2)[N:52]=[CH:51][CH:50]=1)[NH2:44]>C(O)C.C1(C)C=CC=CC=1>[Cl:40][C:41]1[CH:42]=[C:43]([NH:44][C:38]([NH:37][C:35](=[O:36])[C:30]2[CH:29]=[C:28]([CH3:27])[CH:33]=[C:32]([CH3:34])[CH:31]=2)=[S:39])[CH:45]=[CH:46][C:47]=1[O:48][C:49]1[C:58]2[C:53](=[CH:54][C:55]([O:61][CH3:62])=[C:56]([O:59][CH3:60])[CH:57]=2)[N:52]=[CH:51][CH:50]=1

Komponenten

8

Edukt 5

HCID 103563,5-Dimethylbenzoic acidHCID 24386Thionyl ChlorideHCID 810883,5-Dimethylbenzoyl ChlorideHCID 117390273-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]anilineHCID 167756433,5-Dimethyl-1-benzenecarbonyl isothiocyanate

Produkt 1

HCID 21891155N-{3-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-N'-(3,5-dimethylbenzoyl)thioureaAusbeute 97 %

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 3,5-dimethylbenzoic acid (80 mg), and the mixture was heated at 100° C. for one hr. The solvent was removed by distillation, and 3,5-dimethyl-1-benzenecarbonyl isothiocyanate was prepared using the resultant 3,5-dimethyl-1-benzenecarbonyl chloride as a starting compound according to the description of the literature. 3,5-Dimethyl-1-benzenecarbonyl isothiocyanate 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 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 (77 mg, yield 97%).

Aufarbeitung

  1. customThe solvent was removed by distillation, and 3,5-dimethyl-1-benzenecarbonyl 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-96974e3ddf1c426c93785169cc167f33
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07135466B2

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