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

HRID 721868Notes

Reaction equation

HRID 721868 reaction equation
FC1C=CC(C(Cl)=O)=CC=1.[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([N:20]=[C:21]=[S:22])=[O:19])=[CH:14][CH:13]=1.[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:13]=[CH:14][C:15]([C:18]([N:20]=[C:21]=[S:22])=[O:19])=[CH:16][CH:17]=1.[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:15]2[CH:14]=[CH:13][C:12]([F:11])=[CH:17][CH:16]=2)=[S:22])=[C:40]([CH3:45])[CH:39]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 678794-Fluorobenzoyl chlorideHCID 2490894-Fluorobenzoyl isothiocyanateHCID 218905104-((6,7-Dimethoxyquinolin-4-yl)oxy)-2-methylaniline

Product 2

HCID 2490894-Fluorobenzoyl isothiocyanateHCID 21890846N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-methylphenyl}-N'-(4-fluorobenzoyl)thioureaYield 44%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

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-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 (35 mg, yield 44%).

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-cf5b3870ea904da6be1ecb9ad3438c28
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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