Ethanol → N-(4-Chlorobenzoyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]-3-fluorophenyl}thiourea

HRID 721748Notes

Reaction equation

HRID 721748 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][C:17]=1[F:23].C(O)C.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]([N:36]=[C:37]=[S:38])=[O:35])=[CH:30][CH:29]=1>C1(C)C=CC=CC=1>[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]([NH:36][C:37]([NH:20][C:19]2[CH:21]=[CH:22][C:16]([O:15][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][CH:7]=3)=[C:17]([F:23])[CH:18]=2)=[S:38])=[O:35])=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 2321624-Chlorobenzoyl isothiocyanateHCID 114269974-((6,7-Dimethoxyquinolin-4-yl)oxy)-3-fluorobenzenamine

Product 1

HCID 21890834N-(4-Chlorobenzoyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]-3-fluorophenyl}thioureaYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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. Commercially available 4-chloro-1-benzenecarbonyl isothiocyanate (50 μl) 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 (78 mg, yield 96%).

Workup

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

Sources & evidence

ORD record
ord-1e55ebe7fc324d5191eddfb2db66ed93
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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