Methanol → N-{2-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-N'-(2-methylphenyl)urea

HRID 1375795

Reaction equation

HRID 1375795 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([O:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:3]=1[NH2:4].[C:24]1([CH3:33])[C:25]([N:30]=[C:31]=[O:32])=[CH:26][CH:27]=[CH:28][CH:29]=1.CO>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:8]=[C:7]([O:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:3]=1[NH:4][C:31]([NH:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[CH3:33])=[O:32]

Participants

5

Reactant 3

HCID 887MethanolHCID 691942-Tolyl isocyanateHCID 112212234-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-chloroaniline

Product 1

HCID 69353369N-{2-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-N'-(2-methylphenyl)ureaYield 34.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]aniline (122 mg) was dissolved in chloroform (10 ml), and o-toluyl isocyanate (59 mg) was added to the solution. The mixture was stirred at room temperature overnight. Methanol was added to the reaction solution, and the solvent was removed by distillation under the reduced pressure. The residue was dissolved in a minor amount of chloroform, and a large amount of ether was added to the solution to precipitate a crystal. The crystal was collected by filtration to give 59 mg (yield 34%) of the title compound.

Workup

  1. customthe solvent was removed by distillation under the reduced pressure
  2. dissolutionThe residue was dissolved in a minor amount of chloroform
  3. additiona large amount of ether was added to the solution
  4. customto precipitate a crystal
  5. filtrationThe crystal was collected by filtration

Sources & evidence

ORD record
ord-ac0a5a968aad4a758d5dd3661dd92f1c
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Linked notes

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