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5-Hexyn-3-ol → HCID 58738992, Verbindung

HRID 721351
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 721351
[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])=[C:18]([CH3:23])[C:17]=1[CH3:24].Cl[C:26](Cl)([O:28]C(=O)OC(Cl)(Cl)Cl)Cl.[CH3:37][CH2:38][CH:39]([OH:43])[CH2:40][C:41]#[CH:42].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:26](=[O:28])[O:43][CH:39]([CH2:38][CH3:37])[CH2:40][C:41]#[CH:42])=[C:18]([CH3:23])[C:17]=1[CH3:24]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 892235-Hexyn-3-olHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 218904394-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylaniline

Produkt 1

HCID 58738992HCID 58738992, VerbindungAusbeute 62,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140
Toluene
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel
HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2,3-dimethylaniline (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 (68 mg) in methylene chloride was then added thereto, and the mixture was heated under reflux for 10 min. Next, 5-hexyn-3-ol (23 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 (43 mg, yield 59%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-104df43ea6f04e5faed69cdcccb98cbe
Quelldatensatz
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07135466B2

Notizen zur Reaktion

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