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Triethylamine → HCID 19898936, Verbindung

HRID 1196545
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1196545
[CH2:1]([N:8]([C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[CH2:21][O:20]2)=[CH:15][CH:14]=1)[S:9]([CH3:12])(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][NH:23][CH2:24][CH2:25][N:26]1[N:35]=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]1=[O:36].C(N(CC)CC)C>C(O)(C)C>[CH2:1]([N:8]([C:13]1[CH:14]=[CH:15][C:16]([CH:19]([OH:20])[CH2:21][N:23]([CH2:24][CH2:25][N:26]2[N:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]2=[O:36])[CH3:22])=[CH:17][CH:18]=1)[S:9]([CH3:12])(=[O:10])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 198989582-(2-(Methylamino)ethyl)phthalazin-1(2H)-oneHCID 54231897HCID 54231897, Verbindung

Produkt 1

HCID 19898936HCID 19898936, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

2-{4-(N-Benzylmethanesulphonamido)phenyl]oxirane (1.5 g), N-methyl-2-(phthalazin-1-on-2-yl)ethylamine (1.4 g) and triethylamine (1.4 g) in isopropanol (50 ml) were stirred at reflux temperature for 5 hours. The solvent was evaporated, the residue dissolved in methylene chloride and washed three times with sodium carbonate solution and three times with brine. The organic layer was dried and evaporated to give an oil which was purified by column chromatography on silica, "Kieselgel 60" (Merck, Trade Mark), eluting with methylene chloride containing methanol (0% up to 2%). Combination and evaporation of the appropriate fractions gave a foam which was chromatographed a second time on silica, "Kieselgel 60" (Merck, Trade Mark), eluting with methyl isobutyl ketone (MIBK) containing acetone (0% up to 20%). The appropriate fractions were combined and evaporated then re-evaporated from diethyl ether to give the title compound as a foam, yield 450 mg.

Aufarbeitung

  1. temperatureat reflux temperature for 5 hours
  2. customThe solvent was evaporated
  3. dissolutionthe residue dissolved in methylene chloride
  4. washwashed three times with sodium carbonate solution and three times with brine
  5. customThe organic layer was dried
  6. customevaporated
  7. customto give an oil which
  8. customwas purified by column chromatography on silica, "Kieselgel 60" (Merck, Trade Mark)
  9. washeluting with methylene chloride
  10. additioncontaining methanol (0% up to 2%)
  11. customCombination and evaporation of the appropriate fractions
  12. customgave a foam which
  13. customwas chromatographed a second time on silica, "Kieselgel 60" (Merck, Trade Mark)
  14. washeluting with methyl isobutyl ketone (MIBK)
  15. additioncontaining acetone (0% up to 20%)
  16. customevaporated
  17. customthen re-evaporated from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-72f4768b3a2b433580ed7bec69c2d8ba
Quelldatensatz
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05114952

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