2,4-Dichlorophenyl isocyanate → N-(2,4-Dichlorophenyl)-N'-(4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}urea

HRID 1857244Notes

Reaction equation

HRID 1857244 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.[Cl:23][C:24]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:25]=1[N:31]=[C:32]=[O:33]>C1(C)C=CC=CC=1>[Cl:23][C:24]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:25]=1[NH:31][C:32]([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:33]

Participants

4

Reactant 2

HCID 757892,4-Dichlorophenyl isocyanateHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 1

HCID 11225456N-(2,4-Dichlorophenyl)-N'-(4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}ureaYield 85.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (53 mg) was dissolved in toluene (5 ml) with heat, 2,4-dichlorophenyl isocyanate (115 mg) was added, and the admixture was refluxed with heat for 20 minutes. The separated crystals were filtered and then washed with toluene to obtain 74 mg of the title compound (yield: 85%).

Workup

  1. temperaturewith heat
  2. temperaturethe admixture was refluxed
  3. temperaturewith heat for 20 minutes
  4. filtrationThe separated crystals were filtered
  5. washwashed with toluene

Sources & evidence

ORD record
ord-93138775865b49ba8b98f7fb900900bb
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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