p-Isopropylphenyl isocyanate → N-(4-Isopropylphenyl)-N'-{4-[(6,7-dimethoxy-4-quinolinyl)oxy]phenyl}urea

HRID 1857164Notes

Reaction equation

HRID 1857164 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.[CH:23]([C:26]1[CH:31]=[CH:30][C:29]([N:32]=[C:33]=[O:34])=[CH:28][CH:27]=1)([CH3:25])[CH3:24]>C1(C)C=CC=CC=1>[CH:23]([C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:33]([NH:22][C:19]2[CH:18]=[CH:17][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)=[CH:21][CH:20]=2)=[O:34])=[CH:28][CH:27]=1)([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 94416p-Isopropylphenyl isocyanateHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 1

HCID 22132636N-(4-Isopropylphenyl)-N'-{4-[(6,7-dimethoxy-4-quinolinyl)oxy]phenyl}ureaYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (51 mg) was dissolved in toluene (3 ml) with heat, 4-isopropylphenyl isocyanate (0.2 ml) was added, and the admixture was refluxed with heat for 26 minutes. The resulting residue was purified by column chromatography on silica gel eluting with chloroform/acetone (10/1) to obtain 70 mg of the title compound (yield: 90%).

Workup

  1. temperaturewith heat
  2. temperaturethe admixture was refluxed
  3. temperaturewith heat for 26 minutes
  4. customThe resulting residue was purified by column chromatography on silica gel eluting with chloroform/acetone (10/1)

Sources & evidence

ORD record
ord-c227f7421032457ab50b6bb90112a278
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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