Methanol → N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylphenyl}-N'-(2-methylphenyl)urea

HRID 1008370Notes

Reaction equation

HRID 1008370 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])=[C:18]([CH3:23])[C:17]=1[CH3:24].[C:25]1([CH3:34])[C:26]([N:31]=[C:32]=[O:33])=[CH:27][CH:28]=[CH:29][CH:30]=1.CO>C(Cl)(Cl)Cl>[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]([NH:20][C:32]([NH:31][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[CH3:34])=[O:33])=[C:18]([CH3:23])[C:17]=1[CH3:24]

Participants

5

Reactant 3

HCID 887MethanolHCID 691942-Tolyl isocyanateHCID 218904394-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylaniline

Product 1

HCID 22667054N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylphenyl}-N'-(2-methylphenyl)ureaYield 70%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethyl-aniline (120 mg) was dissolved in chloroform (10 ml), and o-toluyl isocyanate (55 μl) 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 which was then collected by filtration to give 130 mg (yield 70%) 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 which
  5. filtrationwas then collected by filtration

Sources & evidence

ORD record
ord-d879ba88edb34b8e871a164509783bfd
Source dataset
uspto-grants-2004_09
Patent number
US06797823B1

Reaction notes

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