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

HRID 721901Notes

Reaction equation

HRID 721901 reaction equation
S(Cl)(Cl)=O.C(C1C=CC(C(O)=O)=CC=1)CCCCCCC.C(C1C=CC(C(Cl)=O)=CC=1)CCCCCCC.[CH3:39][O:40][C:41]1[CH:42]=[C:43]2[C:48](=[CH:49][C:50]=1[O:51][CH3:52])[N:47]=[CH:46][CH:45]=[C:44]2[O:53][C:54]1[CH:60]=[CH:59][C:57]([NH2:58])=[CH:56][CH:55]=1.[CH2:61]([C:69]1[CH:74]=[CH:73][C:72]([C:75]([N:77]=[C:78]=[S:79])=[O:76])=[CH:71][CH:70]=1)[CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH3:68]>C1(C)C=CC=CC=1.C(O)C>[CH3:39][O:40][C:41]1[CH:42]=[C:43]2[C:48](=[CH:49][C:50]=1[O:51][CH3:52])[N:47]=[CH:46][CH:45]=[C:44]2[O:53][C:54]1[CH:60]=[CH:59][C:57]([NH:58][C:78]([NH:77][C:75](=[O:76])[C:72]2[CH:73]=[CH:74][C:69]([CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH3:68])=[CH:70][CH:71]=2)=[S:79])=[CH:56][CH:55]=1

Participants

8

Reactant 5

HCID 19147p-Octylbenzoic acidHCID 24386Thionyl ChlorideHCID 170865Benzoyl chloride, 4-octyl-HCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]anilineHCID 218909734-Octyl-1-benzenecarbonyl isothiocyanate

Product 1

HCID 21890967N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N'-(4-octylbenzoyl)thioureaYield 54%

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 (80 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. 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 (47 mg, yield 54%).

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-cf040ad3b7364b9e86fb4f868873ad89
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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