Thionyl Chloride → N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-fluorophenyl}-N'-[3-(2-methylphenyl)propanoyl]thiourea

HRID 721908

Reaction equation

HRID 721908 reaction equation
S(Cl)(Cl)=O.CC1C=CC=CC=1CCC(O)=O.CC1C=CC=CC=1CCC(Cl)=O.[CH3:29][O:30][C:31]1[CH:32]=[C:33]2[C:38](=[CH:39][C:40]=1[O:41][CH3:42])[N:37]=[CH:36][CH:35]=[C:34]2[O:43][C:44]1[CH:50]=[CH:49][C:47]([NH2:48])=[CH:46][C:45]=1[F:51].[CH3:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=1[CH2:59][CH2:60][C:61]([N:63]=[C:64]=[S:65])=[O:62]>C1(C)C=CC=CC=1.C(O)C>[CH3:29][O:30][C:31]1[CH:32]=[C:33]2[C:38](=[CH:39][C:40]=1[O:41][CH3:42])[N:37]=[CH:36][CH:35]=[C:34]2[O:43][C:44]1[CH:50]=[CH:49][C:47]([NH:48][C:64]([NH:63][C:61](=[O:62])[CH2:60][CH2:59][C:54]2[CH:55]=[CH:56][CH:57]=[CH:58][C:53]=2[CH3:52])=[S:65])=[CH:46][C:45]=1[F:51]

Participants

8

Reactant 5

HCID 24386Thionyl ChlorideHCID 309383-(2-Methylphenyl)propionic acidHCID 114269974-((6,7-Dimethoxyquinolin-4-yl)oxy)-3-fluorobenzenamineHCID 130292013-(2-Methylphenyl)propanoyl chlorideHCID 218907013-(2-Methylphenyl)propanoyl isothiocyanate

Product 1

HCID 21890264N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-fluorophenyl}-N'-[3-(2-methylphenyl)propanoyl]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 3-(2-methylphenyl)propanoic acid (80 mg), and the mixture was heated at 100° C. for one hr. The solvent was removed by distillation, and 3-(2-methylphenyl)propanoyl isothiocyanate was prepared using the resultant 3-(2-methylphenyl)propanoyl chloride as a starting compound according to the description of the literature. 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-fluoroaniline (50 mg) was dissolved in toluene (5 ml) and ethanol (1 ml) to prepare a solution. A solution of 3-(2-methylphenyl)propanoyl 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 (45 mg, yield 54%).

Workup

  1. customThe solvent was removed by distillation, and 3-(2-methylphenyl)propanoyl 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-68e5c7982b5840d4a78c5be050ad1758
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Linked notes

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