Allyl bromide → HCID 12941265, Verbindung

HRID 1277424Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1277424
[CH:1]1([N:7]2[C:11]([CH2:12][CH2:13][CH2:14][O:15][C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[NH:22][C:21](=[O:26])[CH:20]=[CH:19]4)=[N:10][N:9]=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH2:29](Br)[CH:30]=[CH2:31]>CN(C)C=O>[CH2:31]([N:22]1[C:23]2[C:18](=[CH:17][C:16]([O:15][CH2:14][CH2:13][CH2:12][C:11]3[N:7]([CH:1]4[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]4)[N:8]=[N:9][N:10]=3)=[CH:25][CH:24]=2)[CH:19]=[CH:20][C:21]1=[O:26])[CH:30]=[CH2:29]

Komponenten

5

Edukt 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 130210946-[3-(1-Cyclohexyl-1H-tetrazol-5-yl) propoxy]-2(1H)-quinolinone

Produkt 1

HCID 12941265HCID 12941265, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Into 50 ml of dimethylformamide, 1.8 g of 6-[3-(1-cyclohexyltetrazol-5-yl)propoxy]carbostyril is dissolved, then 0.15 g of NaH is added under stirring for 30 minutes by ice-cooling the outside of the reaction vessel. Into the reaction mixture, 0.52 ml of allyl bromide is added dropwise and stirred at a room temperature for 2 hours. The reaction mixture is then concentrated and the residue is extracted with chloroform, washed with water and dried with Na2SO4. After removal of the drying agent by filtration, the mother liquor is concentrated and the residue is dissolved in chloroform. The chloroform solution is washed with water and then concentrated. The residue thus obtained is purified by a silica gel column chromatography [eluent: chloroform-methanol (50:1)]. The eluted solution is concentrated and the residue is recrystallized from chloroform-petroleum ether to obtain 1.2 g of 1-allyl-6-[3-(1-cyclohexyltetrazol-5-yl)propoxy]carbostyril in the form ofcolorless needle-like crystals. Melting point: 102°-103.5° C.

Aufarbeitung

  1. temperaturecooling the outside of the reaction vessel
  2. stirringstirred at a room temperature for 2 hours
  3. concentrationThe reaction mixture is then concentrated
  4. extractionthe residue is extracted with chloroform
  5. washwashed with water
  6. dry with materialdried with Na2SO4
  7. customAfter removal of the drying agent
  8. filtrationby filtration
  9. concentrationthe mother liquor is concentrated
  10. dissolutionthe residue is dissolved in chloroform
  11. washThe chloroform solution is washed with water
  12. concentrationconcentrated
  13. customThe residue thus obtained
  14. customis purified by a silica gel column chromatography [eluent: chloroform-methanol (50:1)]
  15. concentrationThe eluted solution is concentrated
  16. customthe residue is recrystallized from chloroform-petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-0217019033464099a1eda23ef850c3d7
Quelldatensatz
uspto-grants-1981_07
Patentnummer
US04277479

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