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

HRID 1857241Notes

Reaction equation

HRID 1857241 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][CH:27]=[C:26]([CH3:30])[C:25]=1[N:31]=[C:32]=[O:33]>C1(C)C=CC=CC=1>[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[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 2681232-Chloro-6-methylphenyl isocyanateHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 1

HCID 22132630N-(2-Chloro-6-methylphenyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}ureaYield 74%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (52 mg) was dissolved in toluene (5 ml) with heat, 2-chloro-6-methylphenyl isocyanate (0.1 ml) was added, and the admixture was refluxed with heat for 17 minutes. The separated crystals were filtered and then washed with toluene to obtain 61 mg of the title compound (yield: 74%).

Workup

  1. temperaturewith heat
  2. temperaturethe admixture was refluxed
  3. temperaturewith heat for 17 minutes
  4. filtrationThe separated crystals were filtered
  5. washwashed with toluene

Sources & evidence

ORD record
ord-c58514839d4247e0a63197ad345222c9
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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