2,4-Dimethylbenzoic acid → N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N'-(2,4-dimethylbenzoyl)thiourea

HRID 721779

Reaktionsgleichung

Reaktionsgleichung von HRID 721779
S(Cl)(Cl)=O.CC1C=C(C)C=CC=1C(O)=O.CC1C=C(C)C=CC=1C(Cl)=O.[CH3:27][O:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][C:38]=1[O:39][CH3:40])[N:35]=[CH:34][CH:33]=[C:32]2[O:41][C:42]1[CH:48]=[CH:47][C:45]([NH2:46])=[CH:44][CH:43]=1.[CH3:49][C:50]1[CH:55]=[C:54]([CH3:56])[CH:53]=[CH:52][C:51]=1[C:57]([N:59]=[C:60]=[S:61])=[O:58]>C1(C)C=CC=CC=1.C(O)C>[CH3:27][O:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][C:38]=1[O:39][CH3:40])[N:35]=[CH:34][CH:33]=[C:32]2[O:41][C:42]1[CH:48]=[CH:47][C:45]([NH:46][C:60]([NH:59][C:57](=[O:58])[C:51]2[CH:52]=[CH:53][C:54]([CH3:56])=[CH:55][C:50]=2[CH3:49])=[S:61])=[CH:44][CH:43]=1

Komponenten

8

Edukt 5

HCID 118972,4-Dimethylbenzoic acidHCID 24386Thionyl ChlorideHCID 1408672,4-Dimethylbenzoyl chlorideHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]anilineHCID 167781212,4-Dimethyl-1-benzenecarbonyl isothiocyanate

Produkt 1

HCID 21890874N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N'-(2,4-dimethylbenzoyl)thioureaAusbeute 93 %

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 2,4-dimethylbenzoic acid (80 mg), and the mixture was heated at 100° C. for one hr. The solvent was removed by distillation, and 2,4-dimethyl-1-benzenecarbonyl isothiocyanate was prepared using the resultant 2,4-dimethyl-1-benzenecarbonyl chloride as a starting compound according to the description of the literature. 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 2,4-dimethyl-1-benzenecarbonyl isothiocyanate in ethanol (1 ml) was 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 93%).

Aufarbeitung

  1. customThe solvent was removed by distillation, and 2,4-dimethyl-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-e6d68adf7f7b4272ae2936c463fba777
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07135466B2

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