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

HRID 721902

Reaction equation

HRID 721902 reaction equation
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][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:51]=[C:52]([C:57]([N:59]=[C:60]=[S:61])=[O:58])[CH:53]=[C:54]([CH3:56])[CH:55]=1>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:52]2[CH:51]=[C:50]([CH3:49])[CH:55]=[C:54]([CH3:56])[CH:53]=2)=[S:61])=[CH:44][CH:43]=1

Participants

8

Reactant 5

HCID 103563,5-Dimethylbenzoic acidHCID 24386Thionyl ChlorideHCID 810883,5-Dimethylbenzoyl ChlorideHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]anilineHCID 167756433,5-Dimethyl-1-benzenecarbonyl isothiocyanate

Product 1

HCID 21890018N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-phenyl}-N'-(3,5-dimethylbenzoyl)thioureaYield 47%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

Toluene (20 ml) and thionyl chloride (1 ml) was 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. 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 3,5-dimethyl-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 (39 mg, yield 47%).

Workup

  1. customThe solvent was removed by distillation, and 3,5-dimethyl-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-39d7d2021a6c4803a3a713f129fc5114
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Linked notes

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