ethyl N-carbonylcarbamate → N-Ethoxycarbonyl-N'-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}urea

HRID 1857180Notes

Reaction equation

HRID 1857180 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:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1.[CH2:23]([O:25][C:26]([N:28]=[C:29]=[O:30])=[O:27])[CH3:24]>C1(C)C=CC=CC=1>[CH2:23]([O:25][C:26]([NH:28][C:29]([NH:22][C:19]1[CH:18]=[CH:17][C:16]([O:15][C:6]2[C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]=[CH:8][CH:7]=2)=[CH:21][CH:20]=1)=[O:30])=[O:27])[CH3:24]

Participants

4

Reactant 2

HCID 300166ethyl N-carbonylcarbamateHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 1

HCID 22132738N-Ethoxycarbonyl-N'-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}ureaYield 28%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (52 mg) was dissolved in toluene (5 ml) with heat, ethoxycarbonyl isocyanate (0.2 ml) was added, and the admixture was refluxed with heat for 15 minutes. The resulting residue was purified by column chromatography on silica gel eluting with chloroform/acetone (10/1) to obtain 20 mg of the title compound (yield: 28%).

Workup

  1. temperaturewith heat
  2. temperaturethe admixture was refluxed
  3. temperaturewith heat for 15 minutes
  4. customThe resulting residue was purified by column chromatography on silica gel eluting with chloroform/acetone (10/1)

Sources & evidence

ORD record
ord-68ec7c36663b4a8aa0dc51c4ec73c127
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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