4-Fluorobenzoyl chloride → N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N'-(4-fluorobenzoyl)thiourea

HRID 721738Notes

Reaction equation

HRID 721738 reaction equation
FC1C=CC(C(Cl)=O)=CC=1.[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:22]=1[O:23][CH3:24])[N:19]=[CH:18][CH:17]=[C:16]2[O:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1.[F:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]([N:42]=[C:43]=[S:44])=[O:41])=[CH:36][CH:35]=1>C1(C)C=CC=CC=1.C(O)C>[F:33][C:34]1[CH:35]=[CH:36][C:37]([C:40]([N:42]=[C:43]=[S:44])=[O:41])=[CH:38][CH:39]=1.[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:22]=1[O:23][CH3:24])[N:19]=[CH:18][CH:17]=[C:16]2[O:25][C:26]1[CH:32]=[CH:31][C:29]([NH:30][C:43]([NH:42][C:40](=[O:41])[C:37]2[CH:38]=[CH:39][C:34]([F:33])=[CH:35][CH:36]=2)=[S:44])=[CH:28][CH:27]=1

Participants

7

Reactant 3

HCID 678794-Fluorobenzoyl chlorideHCID 2490894-Fluorobenzoyl isothiocyanateHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 2

HCID 2490894-Fluorobenzoyl isothiocyanateHCID 21890466N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N'-(4-fluorobenzoyl)thioureaYield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent

Procedure

4-Fluoro-1-benzenecarbonyl isothiocyanate was prepared using commercially available 4-fluoro-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 4-fluoro-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 (69 mg, yield 85%).

Workup

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

Sources & evidence

ORD record
ord-1c00d36ff6e546aebd7498b4042b342d
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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