2,4-Dimethoxybenzoyl chloride → N-(2,4-Dimethoxybenzoyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}thiourea

HRID 721893Notes

Reaction equation

HRID 721893 reaction equation
COC1C=C(OC)C=CC=1C(Cl)=O.[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][C:25]=1[O:26][CH3:27])[N:22]=[CH:21][CH:20]=[C:19]2[O:28][C:29]1[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=1.[CH3:36][O:37][C:38]1[CH:43]=[C:42]([O:44][CH3:45])[CH:41]=[CH:40][C:39]=1[C:46]([N:48]=[C:49]=[S:50])=[O:47]>C1(C)C=CC=CC=1.C(O)C>[CH3:36][O:37][C:38]1[CH:43]=[C:42]([O:44][CH3:45])[CH:41]=[CH:40][C:39]=1[C:46]([N:48]=[C:49]=[S:50])=[O:47].[CH3:36][O:37][C:38]1[CH:43]=[C:42]([O:44][CH3:45])[CH:41]=[CH:40][C:39]=1[C:46]([NH:48][C:49]([NH:33][C:32]1[CH:34]=[CH:35][C:29]([O:28][C:19]2[C:18]3[C:23](=[CH:24][C:25]([O:26][CH3:27])=[C:16]([O:15][CH3:14])[CH:17]=3)[N:22]=[CH:21][CH:20]=2)=[CH:30][CH:31]=1)=[S:50])=[O:47]

Participants

7

Reactant 3

HCID 27347192,4-Dimethoxybenzoyl chlorideHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]anilineHCID 21890675HCID 21890675, compound

Product 2

HCID 21890379N-(2,4-Dimethoxybenzoyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}thioureaYield 48%HCID 21890675HCID 21890675, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent

Procedure

2,4-Dimethoxy-1-benzenecarbonyl isothiocyanate was prepared using commercially available 2,4-dimethoxy-1-benzenecarbonyl 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 2,4-dimethoxy-1-benzenecarbonyl 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 (42 mg, yield 48%).

Workup

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

Sources & evidence

ORD record
ord-ce72f3741b7e47db8709083fbf0ba38c
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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