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

HRID 721801

Reaction equation

HRID 721801 reaction equation
S(Cl)(Cl)=O.COC1C=CC=CC=1CCC(O)=O.COC1C=CC=CC=1CCC(Cl)=O.[CH3:31][O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH2:39][CH2:40][C:41]([N:43]=[C:44]=[S:45])=[O:42].[CH3:46][O:47][C:48]1[CH:49]=[C:50]2[C:55](=[CH:56][C:57]=1[O:58][CH3:59])[N:54]=[CH:53][CH:52]=[C:51]2[O:60][C:61]1[CH:67]=[CH:66][C:64]([NH2:65])=[CH:63][CH:62]=1>C(O)C.C1(C)C=CC=CC=1>[CH3:46][O:47][C:48]1[CH:49]=[C:50]2[C:55](=[CH:56][C:57]=1[O:58][CH3:59])[N:54]=[CH:53][CH:52]=[C:51]2[O:60][C:61]1[CH:62]=[CH:63][C:64]([NH:65][C:44]([NH:43][C:41](=[O:42])[CH2:40][CH2:39][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[O:32][CH3:31])=[S:45])=[CH:66][CH:67]=1

Participants

8

Reactant 5

HCID 24386Thionyl ChlorideHCID 806523-(o-Methoxyphenyl)propionic acidHCID 27597143-(2-Methoxyphenyl)propanoyl chlorideHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]anilineHCID 218900643-(2-Methoxyphenyl)propanoyl isothiocyanate

Product 1

HCID 21889943N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N'-[3-(2-methoxyphenyl)propanoyl]thioureaYield 74%

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-methoxyphenyl)propanoic acid (80 mg), and the mixture was heated at 100° C. for one hr. The solvent was removed by distillation, and 3-(2-methoxyphenyl)propanoyl isothiocyanate was prepared using the resultant 3-(2-methoxyphenyl)propanoyl chloride as a starting compound according to the description of the literature. 3-(2-Methoxyphenyl)propanoyl isothiocyanate was dissolved in ethanol (1 ml) to prepare a solution. 4-[(6,7-Dimethoxy-4-quinolyl)oxy]aniline (50 mg), toluene (5 ml), and ethanol (1 ml) were 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 (60 mg, yield 74%).

Workup

  1. customThe solvent was removed by distillation, and 3-(2-methoxyphenyl)propanoyl isothiocyanate
  2. customwas prepared
  3. customto prepare a solution
  4. concentrationThe reaction solution was concentrated
  5. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-0553ed0c4f6a448b8c4e297d76b3b3e0
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Linked notes

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