p-Octylbenzoic acid → N-{3-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-N'-(4-octylbenzoyl)thiourea

HRID 721961Notes

Reaction equation

HRID 721961 reaction equation
S(Cl)(Cl)=O.C(C1C=CC(C(O)=O)=CC=1)CCCCCCC.C(C1C=CC(C(Cl)=O)=CC=1)CCCCCCC.[Cl:39][C:40]1[CH:41]=[C:42]([CH:44]=[CH:45][C:46]=1[O:47][C:48]1[C:57]2[C:52](=[CH:53][C:54]([O:60][CH3:61])=[C:55]([O:58][CH3:59])[CH:56]=2)[N:51]=[CH:50][CH:49]=1)[NH2:43].[CH2:62]([C:70]1[CH:75]=[CH:74][C:73]([C:76]([N:78]=[C:79]=[S:80])=[O:77])=[CH:72][CH:71]=1)[CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH3:69]>C1(C)C=CC=CC=1.C(O)C>[Cl:39][C:40]1[CH:41]=[C:42]([NH:43][C:79]([NH:78][C:76](=[O:77])[C:73]2[CH:74]=[CH:75][C:70]([CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH3:69])=[CH:71][CH:72]=2)=[S:80])[CH:44]=[CH:45][C:46]=1[O:47][C:48]1[C:57]2[C:52](=[CH:53][C:54]([O:60][CH3:61])=[C:55]([O:58][CH3:59])[CH:56]=2)[N:51]=[CH:50][CH:49]=1

Participants

8

Reactant 5

HCID 19147p-Octylbenzoic acidHCID 24386Thionyl ChlorideHCID 170865Benzoyl chloride, 4-octyl-HCID 117390273-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]anilineHCID 218909734-Octyl-1-benzenecarbonyl isothiocyanate

Product 1

HCID 21890818N-{3-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-N'-(4-octylbenzoyl)thioureaYield 58%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

Toluene (20 ml) and thionyl chloride (1 ml) were added to commercially available 4-octylbenzoic acid (40 mg), and the mixture was heated at 100° C. for one hr. The solvent was removed by distillation, and 4-octyl-1-benzenecarbonyl isothiocyanate was prepared using the resultant 4-octyl-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-octyl-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 (53 mg, yield 58%).

Workup

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

Sources & evidence

ORD record
ord-f733f7bfb067432b870060d7f83b7889
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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