p,alpha-DIMETHYLBENZYL ALCOHOL → 1-(4-Methylphenyl)ethyl N-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}carbamate

HRID 721089

Reaktionsgleichung

Reaktionsgleichung von HRID 721089
[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.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][C:50]1[CH:58]=[CH:57][C:53]([CH:54]([OH:56])[CH3:55])=[CH:52][CH:51]=1>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][CH:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][C:38](=[O:40])[O:56][CH:54]([C:53]2[CH:57]=[CH:58][C:50]([CH3:49])=[CH:51][CH:52]=2)[CH3:55])=[CH:18][CH:17]=1

Komponenten

6

Edukt 4

HCID 10817p,alpha-DIMETHYLBENZYL ALCOHOLHCID 94429TriphosgeneHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]anilineHCID 22504574Toluene triethylamine

Produkt 1

HCID 218899921-(4-Methylphenyl)ethyl N-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}carbamateAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-[(6,7-Dimethoxy-4-quinolyl)oxy]aniline (72 mg) was added to toluene/triethylamine=10/1 (7 ml), and the mixture was heated under reflux to prepare a solution. A solution of triphosgene (109 mg) in methylene chloride was then added to the solution, and the mixture was heated under reflux for 15 min. Subsequently 4-methyl-α-methylbenzyl alcohol (50 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 (98 mg, yield 81%)

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-315be8aeb4884c55b336198a8a961c6d
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07135466B2

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