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

HRID 1857239Notes

Reaction equation

HRID 1857239 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]([N+:30]([O-:32])=[O:31])[CH:27]=[CH:26][C:25]=1[N:33]=[C:34]=[O:35]>C1(C)C=CC=CC=1>[Cl:23][C:24]1[CH:29]=[C:28]([N+:30]([O-:32])=[O:31])[CH:27]=[CH:26][C:25]=1[NH:33][C:34]([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:35]

Participants

4

Reactant 2

HCID 46142212-Chloro-4-nitrophenyl isocyanateHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 1

HCID 22132755N-(2-Chloro-4-nitrophenyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}ureaYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (104 mg) was dissolved in toluene (10 ml) with heat, 2-chloro-4-nitrophenyl isocyanate (150 mg) was added, and the admixture was refluxed with heat for 10 minutes. The separated crystals were filtered and then washed with toluene to obtain 172 mg of the title compound (yield: 100%).

Workup

  1. temperaturewith heat
  2. temperaturethe admixture was refluxed
  3. temperaturewith heat for 10 minutes
  4. filtrationThe separated crystals were filtered
  5. washwashed with toluene

Sources & evidence

ORD record
ord-5a3db80752e64930aa9e3bf0a86418ad
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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