o-Butyl-aniline → N-(2-n-Butylphenyl)-N'-(4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}urea

HRID 1857247노트

반응식

HRID 1857247 반응식
[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.[CH2:35]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[NH2:45])[CH2:36][CH2:37][CH3:38].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C(N(CC)CC)C>[CH2:35]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[NH:45][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])[CH2:36][CH2:37][CH3:38]

참가 물질

7

반응물 4

HCID 75909o-Butyl-anilineHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

생성물 1

HCID 22132676N-(2-n-Butylphenyl)-N'-(4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}urea수율 69%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8471Triethylamine용매

실험 절차

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (119 mg) was suspended in toluene (12 ml), after the addition of triethylamine (2.4 ml), triphosgene (133 mg) was added, and the admixture was refluxed with heat for 2 minutes. 2-n-Butylphenylamine (0.13 ml) was added to the reaction mixture, and the admixture was refluxed with heat for 10 minutes. After the addition of aqueous sodium hydrogen carbonate, the reaction mixture was extracted 2 times with chloroform, 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 (4/1) to obtain 130 mg of the title compound (yield: 69%).

후처리

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

출처 및 근거

ORD 기록
ord-d2d250d821c44616b460e2a8657a87a0
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06143764

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