3-(Trifluoromethyl)benzoyl chloride → N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-fluorophenyl}-N'-[3-(trifluoromethyl)benzoyl]thiourea

HRID 721725Notes

Reaction equation

HRID 721725 reaction equation
FC(F)(F)C1C=C(C(Cl)=O)C=CC=1.[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][C:30]=1[F:36].[F:37][C:38]([F:51])([F:50])[C:39]1[CH:40]=[C:41]([C:45]([N:47]=[C:48]=[S:49])=[O:46])[CH:42]=[CH:43][CH:44]=1>C1(C)C=CC=CC=1.C(O)C>[F:50][C:38]([F:37])([F:51])[C:39]1[CH:40]=[C:41]([C:45]([N:47]=[C:48]=[S:49])=[O:46])[CH:42]=[CH:43][CH:44]=1.[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]([NH:33][C:48]([NH:47][C:45](=[O:46])[C:41]2[CH:42]=[CH:43][CH:44]=[C:39]([C:38]([F:37])([F:51])[F:50])[CH:40]=2)=[S:49])=[CH:31][C:30]=1[F:36]

Participants

7

Reactant 3

HCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 114269974-((6,7-Dimethoxyquinolin-4-yl)oxy)-3-fluorobenzenamineHCID 217841763-(trifluoromethyl)benzoyl isothiocyanate

Product 2

HCID 217841763-(trifluoromethyl)benzoyl isothiocyanateHCID 21890662N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-fluorophenyl}-N'-[3-(trifluoromethyl)benzoyl]thioureaYield 89%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent

Procedure

3-(Trifluoromethyl)-1-benzenecarbonyl isothiocyanate was prepared using commercially available 3-(trifluoromethyl)-1-benzenecarbonyl chloride (80 mg) as a starting compound according to the description of the literature. 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-fluoroaniline (50 mg) was dissolved in toluene (5 ml) and ethanol (1 ml) to prepare a solution. A solution of 3-(trifluoromethyl)-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 (77 mg, yield 89%).

Workup

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

Sources & evidence

ORD record
ord-d979ad386c734b44bebb2867f65873fd
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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