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

HRID 1857257Notes

Reaction equation

HRID 1857257 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]([CH3:33])[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]([CH3:33])[CH:25]=1

Participants

4

Reactant 2

HCID 1421574-Chloro-2-methylphenyl isocyanateHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 1

HCID 22132705N-(4-Chloro-2-methylphenyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}ureaYield 80.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (55 mg) was dissolved in toluene (5 ml) with heat, 4-chloro-2-methylphenyl isocyanate (90 mg) was added, and the admixture was refluxed with heat for 26 minutes. The separated crystals were filtered and then washed with toluene to obtain 69 mg of the title compound (yield: 80%).

Workup

  1. temperaturewith heat
  2. temperaturethe admixture was refluxed
  3. temperaturewith heat for 26 minutes
  4. filtrationThe separated crystals were filtered
  5. washwashed with toluene

Sources & evidence

ORD record
ord-2f38c2c835cf4b7ab227253f2da26e64
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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