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

HRID 721951Notes

Reaction equation

HRID 721951 reaction equation
[CH3:1]OC1C=C(OC)C=CC=1C(Cl)=O.[Cl:14][C:15]1[CH:21]=[C:20]([O:22][C:23]2[C:32]3[C:27](=[CH:28][C:29]([O:35][CH3:36])=[C:30]([O:33][CH3:34])[CH:31]=3)[N:26]=[CH:25]N=2)[CH:19]=[CH:18][C:16]=1[NH2:17].[CH3:37][O:38][C:39]1[CH:44]=[C:43]([O:45][CH3:46])[CH:42]=[CH:41][C:40]=1[C:47]([N:49]=[C:50]=[S:51])=[O:48]>C1(C)C=CC=CC=1.C(O)C>[CH3:37][O:38][C:39]1[CH:44]=[C:43]([O:45][CH3:46])[CH:42]=[CH:41][C:40]=1[C:47]([N:49]=[C:50]=[S:51])=[O:48].[Cl:14][C:15]1[CH:21]=[C:20]([O:22][C:23]2[C:32]3[C:27](=[CH:28][C:29]([O:35][CH3:36])=[C:30]([O:33][CH3:34])[CH:31]=3)[N:26]=[CH:25][CH:1]=2)[CH:19]=[CH:18][C:16]=1[NH:17][C:50]([NH:49][C:47](=[O:48])[C:40]1[CH:41]=[CH:42][C:43]([O:45][CH3:46])=[CH:44][C:39]=1[O:38][CH3:37])=[S:51]

Participants

7

Reactant 3

HCID 27347192,4-Dimethoxybenzoyl chlorideHCID 218898992-Chloro-4-((6,7-dimethoxyquinazolin-4-yl)oxy)anilineHCID 21890675HCID 21890675, compound

Product 2

HCID 21890043N-{2-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-N'-(2,4-dimethoxybenzoyl)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. 2-Chloro-4-[(6,7-Dimethoxy-4-quinazolinyl)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 (40 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-781bcc35f20443d6bda4589066050ff0
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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