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

HRID 1857253Notes

Reaction equation

HRID 1857253 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]=[CH:28][C:27]([N:30]=[C:31]=[O:32])=[C:26]([N+:33]([O-:35])=[O:34])[CH:25]=1>C1(C)C=CC=CC=1>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31]([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:32])=[C:26]([N+:33]([O-:35])=[O:34])[CH:25]=1

Participants

4

Reactant 2

HCID 42472574-Chloro-2-nitrophenyl isocyanateHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 1

HCID 22132647N-(4-Chloro-2-nitrophenyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}ureaYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (123 mg) was dissolved in toluene (12 ml) with heat, 4-chloro-2-nitrophenyl isocyanate (172 mg) was added, and the admixture was refluxed with heat for 14 minutes. The separated crystals were filtered and then washed with toluene to obtain 174 mg of the title compound (yield: 85%).

Workup

  1. temperaturewith heat
  2. temperaturethe admixture was refluxed
  3. temperaturewith heat for 14 minutes
  4. filtrationThe separated crystals were filtered
  5. washwashed with toluene

Sources & evidence

ORD record
ord-ecca966c00e14bdda99cd97484f9fd01
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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