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4-Heptanol → 1-Propylbutyl N-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}carbamate

HRID 721273
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HRID 721273 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:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1.Cl[C:24](Cl)([O:26]C(=O)OC(Cl)(Cl)Cl)Cl.[CH3:35][CH2:36][CH2:37][CH:38]([OH:42])[CH2:39][CH2:40][CH3:41].C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(N(CC)CC)C.C1(C)C=CC=CC=1>[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:22]=[CH:21][C:19]([NH:20][C:24](=[O:26])[O:42][CH:38]([CH2:39][CH2:40][CH3:41])[CH2:37][CH2:36][CH3:35])=[CH:18][CH:17]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 115134-HeptanolHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

생성물 1

HCID 218901251-Propylbutyl N-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}carbamate수율 64.9%

시약·촉매·용매 3

HCID 1140
Toluene
용매
HCID 6344Dichloromethane용매
HCID 8471Triethylamine용매

실험 절차

4-[(6,7-Dimethoxy-4-quinolyl)oxy]aniline (50 mg) was added to toluene (5 ml), and triethylamine (0.5 ml), and the mixture was heated under reflux to prepare a solution. A solution of triphosgene (77 mg) in methylene chloride was then added thereto, and the mixture was heated under reflux for 10 min. Next, 4-heptanol (30 mg) was added thereto, and the mixture was further stirred with heating under reflux for 3 hr. A saturated aqueous sodium bicarbonate solution was added to stop the reaction, and the reaction solution was then extracted with chloroform, followed by washing with a 1 N aqueous hydrochloric acid solution, water, and saturated brine in that order. The extract was dried over sodium sulfate and was then concentrated. The residue was purified on a column using chloroform/methanol to give the title compound (48 mg, yield 60%).

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. customto prepare a solution
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 10 min
  6. temperaturewith heating
  7. temperatureunder reflux for 3 hr
  8. customthe reaction
  9. extractionthe reaction solution was then extracted with chloroform
  10. washby washing with a 1 N aqueous hydrochloric acid solution, water, and saturated brine in that order
  11. dry with materialThe extract was dried over sodium sulfate
  12. concentrationwas then concentrated
  13. customThe residue was purified on a column

출처 및 근거

ORD 기록
ord-5457673f2b594655beeaa94db76f8ebc
출처 데이터셋
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07135466B2

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