Toluene → N-(3,5-Dichlorobenzoyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}thiourea

HRID 721785Notes

Reaction equation

HRID 721785 reaction equation
ClC1C=C(C(Cl)=O)C=C(Cl)C=1.[Cl:12][C:13]1[CH:14]=[C:15]([C:20]([N:22]=[C:23]=[S:24])=[O:21])[CH:16]=[C:17]([Cl:19])[CH:18]=1.[CH3:25][O:26][C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][C:36]=1[O:37][CH3:38])[N:33]=[CH:32][CH:31]=[C:30]2[O:39][C:40]1[CH:46]=[CH:45][C:43]([NH2:44])=[CH:42][CH:41]=1.C1(C)C=CC=CC=1>C(O)C>[Cl:12][C:13]1[CH:14]=[C:15]([C:20]([N:22]=[C:23]=[S:24])=[O:21])[CH:16]=[C:17]([Cl:19])[CH:18]=1.[Cl:12][C:13]1[CH:14]=[C:15]([CH:16]=[C:17]([Cl:19])[CH:18]=1)[C:20]([NH:22][C:23]([NH:44][C:43]1[CH:45]=[CH:46][C:40]([O:39][C:30]2[C:29]3[C:34](=[CH:35][C:36]([O:37][CH3:38])=[C:27]([O:26][CH3:25])[CH:28]=3)[N:33]=[CH:32][CH:31]=2)=[CH:41][CH:42]=1)=[S:24])=[O:21]

Participants

7

Reactant 4

HCID 1140TolueneHCID 761913,5-Dichlorobenzoyl chlorideHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]anilineHCID 16774862HCID 16774862, compound

Product 2

HCID 16774862HCID 16774862, compoundHCID 21890393N-(3,5-Dichlorobenzoyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}thioureaYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

3,5-Dichloro-1-benzenecarbonyl isothiocyanate was prepared using commercially available 3,5-dichloro-1-benzenecarbonyl chloride (80 mg) as a starting compound according to the description of the literature. 3,5-Dichloro-1-benzenecarbonyl 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 (73 mg, yield 79%). Mass spectrometry value (ESI-MS, m/z): 529 (M++1)

Workup

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

Sources & evidence

ORD record
ord-e05e88b7dfc34ff896c180a1b5524bd8
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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