Triphosgene → N-(2,4,5-Trifluorophenyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}urea

HRID 1857269Notes

Reaction equation

HRID 1857269 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.ClC(Cl)(O[C:27](=[O:33])OC(Cl)(Cl)Cl)Cl.[F:35][C:36]1[CH:42]=[C:41]([F:43])[C:40]([F:44])=[CH:39][C:37]=1[NH2:38].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C(N(CC)CC)C>[F:35][C:36]1[CH:42]=[C:41]([F:43])[C:40]([F:44])=[CH:39][C:37]=1[NH:38][C:27]([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

7

Reactant 4

HCID 94429TriphosgeneHCID 949532,4,5-TrifluoroanilineHCID 516892Sodium BicarbonateHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 1

HCID 22132701N-(2,4,5-Trifluorophenyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}ureaYield 73.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8471TriethylamineSolvent

Procedure

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (50 mg) was dissolved in toluene (5 ml) with heat, after the addition of triethylamine (1 ml), triphosgene (55 mg) was added, and the admixture was refluxed with heat for 3 minutes. 2,4,5-Trifluoroaniline (75 mg) was added to the reaction mixture, and the admixture was refluxed with heat for 20 minutes. After the addition of aqueous sodium hydrogen carbonate, the reaction mixture was extracted 2 times with ethyl acetate, and the organic layer was then washed with brine and dried with anhydrous sodium sulfate. The solvent was removed by reduced-pressure distillation, and the resulting residue was purified by column chromatography on silica gel eluting with chloroform/acetone (10/1) to obtain 58 mg of the title compound (yield: 73%).

Workup

  1. temperaturewith heat
  2. additionwas added
  3. temperaturethe admixture was refluxed
  4. temperaturewith heat for 3 minutes
  5. temperaturethe admixture was refluxed
  6. temperaturewith heat for 20 minutes
  7. extractionthe reaction mixture was extracted 2 times with ethyl acetate
  8. washthe organic layer was then washed with brine
  9. dry with materialdried with anhydrous sodium sulfate
  10. customThe solvent was removed by reduced-pressure distillation
  11. customthe resulting residue was purified by column chromatography on silica gel eluting with chloroform/acetone (10/1)

Sources & evidence

ORD record
ord-40fbba2c309145c8b7b78b1563566c7e
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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