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

HRID 1857250Notes

Reaction equation

HRID 1857250 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 73%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (58 mg) was dissolved in toluene (5 ml) with heat, 2,4-dichlorophenyl isocyanate (93 mg) was added, and the admixture was refluxed with heat for 20 minutes. The reaction solution was purified by column chromatography on silica gel eluting with chloroform/acetone (10/1) to obtain 69 mg of the title compound (yield: 73%).

Workup

  1. temperaturewith heat
  2. temperaturethe admixture was refluxed
  3. temperaturewith heat for 20 minutes
  4. customThe reaction solution was purified by column chromatography on silica gel eluting with chloroform/acetone (10/1)

Sources & evidence

ORD record
ord-dc66b5ef4afe4b7dbcf46e826a1b9095
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

Loading…