Toluene → N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-methylphenyl}-N'-(2-fluorobenzoyl)thiourea

HRID 721869Notes

Reaction equation

HRID 721869 reaction equation
FC1C=CC=CC=1C(Cl)=O.[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([N:20]=[C:21]=[S:22])=[O:19].[CH3:23][O:24][C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][C:34]=1[O:35][CH3:36])[N:31]=[CH:30][CH:29]=[C:28]2[O:37][C:38]1[CH:44]=[CH:43][C:41]([NH2:42])=[C:40]([CH3:45])[CH:39]=1.C1(C)C=CC=CC=1>C(O)C>[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([N:20]=[C:21]=[S:22])=[O:19].[CH3:23][O:24][C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][C:34]=1[O:35][CH3:36])[N:31]=[CH:30][CH:29]=[C:28]2[O:37][C:38]1[CH:44]=[CH:43][C:41]([NH:42][C:21]([NH:20][C:18](=[O:19])[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[F:11])=[S:22])=[C:40]([CH3:45])[CH:39]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 98082-Fluorobenzoyl chlorideHCID 156505082-Fluorobenzoyl isothiocyanateHCID 218905104-((6,7-Dimethoxyquinolin-4-yl)oxy)-2-methylaniline

Product 2

HCID 156505082-Fluorobenzoyl isothiocyanateHCID 21890283N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-methylphenyl}-N'-(2-fluorobenzoyl)thioureaYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-Fluoro-1-benzenecarbonyl isothiocyanate was prepared using commercially available 2-fluoro-1-benzenecarbonyl chloride (80 mg) as a starting compound according to the description of the literature. 2-Fluoro-1-benzenecarbonyl isothiocyanate was dissolved in ethanol (1 ml) to prepare a solution. 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-methylaniline (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 (41 mg, yield 52%).

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-433ff339f75f4152a3705b5da99e287c
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

Loading…