Triphosgene → 2-Methyl-1-phenylpropyl N-{4-[(6,7-dimethoxy-4-quinazolinyl)oxy]phenyl}carbamate

HRID 721144

반응식

HRID 721144 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][N:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1.C1(C)C=CC=CC=1.C(N(CC)CC)C.Cl[C:38](Cl)([O:40]C(=O)OC(Cl)(Cl)Cl)Cl.[CH3:49][CH:50]([CH3:59])[CH:51]([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[OH:52]>C(Cl)Cl>[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][N:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:38](=[O:40])[O:52][CH:51]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[CH:50]([CH3:59])[CH3:49])=[CH:18][CH:17]=1

참가 물질

6

반응물 4

HCID 94429TriphosgeneHCID 956262-Methyl-1-phenyl-1-propanolHCID 116163634-(6,7-Dimethoxyquinazolin-4-yloxy)anilineHCID 22504574Toluene triethylamine

생성물 1

HCID 587389902-Methyl-1-phenylpropyl N-{4-[(6,7-dimethoxy-4-quinazolinyl)oxy]phenyl}carbamate수율 31.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]aniline (75 mg) was added to toluene/triethylamine=10/1 (8 ml), and the mixture was heated under reflux to prepare a solution. A solution of triphosgene (137 mg) in methylene chloride was then added to the solution, and the mixture was heated under reflux for 15 min. Subsequently, 2-methyl-1-phenyl-1-propanol (56 mg) was added thereto, and the mixture was further stirred with heating under reflux for 2 hr. After the completion of the reaction, the reaction solution was allowed to cool to room temperature before distilled water was added thereto. The mixture was subjected to separatory extraction with chloroform, followed by washing with a 1 N aqueous hydrochloric acid solution and saturated brine. The washed solution was dried over sodium sulfate and was concentrated. The residue was purified on a column using chloroform/methanol to give the title compound (38 mg, yield 29%).

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. customto prepare a solution
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 15 min
  6. temperaturewith heating
  7. temperatureunder reflux for 2 hr
  8. customAfter the completion of the reaction
  9. distillationbefore distilled water
  10. additionwas added
  11. extractionThe mixture was subjected to separatory extraction with chloroform
  12. washby washing with a 1 N aqueous hydrochloric acid solution and saturated brine
  13. dry with materialThe washed solution was dried over sodium sulfate
  14. concentrationwas concentrated
  15. customThe residue was purified on a column

출처 및 근거

ORD 기록
ord-c259a294041043319f0602b91fef74ee
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07135466B2

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