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

HRID 721686Notes

Reaction equation

HRID 721686 reaction equation
FC1C=CC=CC=1C(Cl)=O.[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])=[C:28]([F:33])[CH:27]=1.[F:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[C:41]([N:43]=[C:44]=[S:45])=[O:42]>C1(C)C=CC=CC=1.C(O)C>[F:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[C:41]([N:43]=[C:44]=[S:45])=[O:42].[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:44]([NH:43][C:41](=[O:42])[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[F:34])=[S:45])=[C:28]([F:33])[CH:27]=1

Participants

7

Reactant 3

HCID 98082-Fluorobenzoyl chlorideHCID 113014704-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroanilineHCID 156505082-Fluorobenzoyl isothiocyanate

Product 2

HCID 156505082-Fluorobenzoyl isothiocyanateHCID 21890829N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluorophenyl}-N'-(2-fluorobenzoyl)thioureaYield 80%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent

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. 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline (50 mg) was dissolved in toluene (5 ml) and ethanol (1 ml) to prepare a solution. A solution of 2-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 (63 mg, yield 80%).

Workup

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

Sources & evidence

ORD record
ord-65696927965748578d97b00e30d452af
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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