4-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline → N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N'-[3-(methylsulphenyl)propanoyl]thiourea

HRID 721909Notes

Reaction equation

HRID 721909 reaction equation
CSCCC(Cl)=O.[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:19]=1[O:20][CH3:21])[N:16]=[CH:15][CH:14]=[C:13]2[O:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1.[CH3:30][S:31][CH2:32][CH2:33][C:34]([N:36]=[C:37]=[S:38])=[O:35]>C1(C)C=CC=CC=1.C(O)C>[CH3:30][S:31][CH2:32][CH2:33][C:34]([N:36]=[C:37]=[S:38])=[O:35].[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:19]=1[O:20][CH3:21])[N:16]=[CH:15][CH:14]=[C:13]2[O:22][C:23]1[CH:29]=[CH:28][C:26]([NH:27][C:37]([NH:36][C:34](=[O:35])[CH2:33][CH2:32][S:31][CH3:30])=[S:38])=[CH:25][CH:24]=1

Participants

7

Reactant 3

HCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]anilineHCID 129214403-(Methylthio)propionyl ChlorideHCID 218900903-(Methylsulfanyl)propanoyl isothiocyanate

Product 2

HCID 218900903-(Methylsulfanyl)propanoyl isothiocyanateHCID 21891164N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N'-[3-(methylsulphenyl)propanoyl]thioureaYield 56%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent

Procedure

3-(Methylsulphenyl)propanoyl isothiocyanate was prepared using commercially available 3-(methylsulphenyl)propanoyl chloride (80 mg) 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-(methylsulphenyl)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 (41 mg, yield 56%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-faf9a0a4da704fe58562b1a19bd02ba7
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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