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

HRID 721915Notes

Reaction equation

HRID 721915 reaction equation
S(Cl)(Cl)=O.COC1C=CC=CC=1CCC(O)=O.C1(CCCC(Cl)=O)C=CC=CC=1.[CH3:30][O:31][C:32]1[CH:33]=[C:34]2[C:39](=[CH:40][C:41]=1[O:42][CH3:43])[N:38]=[CH:37][CH:36]=[C:35]2[O:44][C:45]1[CH:50]=[CH:49][C:48]([NH:51][CH2:52][CH3:53])=[CH:47][CH:46]=1.[CH3:54][O:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][C:57]=1[CH2:62][CH2:63][C:64]([N:66]=[C:67]=[S:68])=[O:65]>C1(C)C=CC=CC=1.C(O)C>[CH3:30][O:31][C:32]1[CH:33]=[C:34]2[C:39](=[CH:40][C:41]=1[O:42][CH3:43])[N:38]=[CH:37][CH:36]=[C:35]2[O:44][C:45]1[CH:50]=[CH:49][C:48]([N:51]([CH2:52][CH3:53])[C:67]([NH:66][C:64](=[O:65])[CH2:63][CH2:62][C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][C:56]=2[O:55][CH3:54])=[S:68])=[CH:47][CH:46]=1

Participants

8

Reactant 5

HCID 24386Thionyl ChlorideHCID 806523-(o-Methoxyphenyl)propionic acidHCID 117898654-Phenylbutanoyl ChlorideHCID 218900643-(2-Methoxyphenyl)propanoyl isothiocyanateHCID 21891226N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N-ethylamine

Product 1

HCID 21891057N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N-ethyl-N'-[3-(2-methoxyphenyl)propanoyl]thioureaYield 52%

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 4-phenylbutanoyl chloride as a starting compound according to the description of the literature. N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N-ethylamine (50 mg) was dissolved in toluene (5 ml) and ethanol (1 ml) to prepare a solution. A solution of 3-(2-methoxyphenyl)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 (44 mg, yield 52%).

Workup

  1. customThe solvent was removed by distillation, and 3-(2-methoxyphenyl)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-0b8a5a599c614390bb76d4da292ab919
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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