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Diisopropylethylamine → HCID 86606414, Verbindung

HRID 2421509
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2421509
[CH3:1][O:2][C:3]([C:5]1[C:9]([C:10](Cl)=[O:11])=[N:8][N:7]([CH3:13])[N:6]=1)=[O:4].C(N(C(C)C)C(C)C)C>C1COCC1.C(OCC)(=O)C.[Pd]>[CH3:1][O:2][C:3]([C:5]1[C:9]([CH:10]=[O:11])=[N:8][N:7]([CH3:13])[N:6]=1)=[O:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 81531DiisopropylethylamineHCID 86606415HCID 86606415, Verbindung

Produkt 1

HCID 86606414HCID 86606414, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl Acetate
Lösungsmittel

Versuchsvorschrift

To a solution of freshly prepared 5-Chlorocarbonyl-2-methyl-2H-1,2,3-triazole-4-carboxylic acid methyl ester (2.7 g; ca. 13 mmol) in THF (270 ml) was added ethyl-diisopropyl-amine (1.88 g; 1.1 eq.). The mixture was hydrogenated in the presence of 2.7 g 10% Pd/C at 0-5° C. at normal pressure for 2½ hours and subsequently filtered from the catalyst. The clear solution was evaporated to give the crude as a solid which was dissolved again in ethyl acetate and stirred for a couple of minutes with silica gel. After filtration and evaporation 1.77 g (84%) of pure product as off-white crystals were obtained [m.p. 107-108° C.; 1H-NMR (300 MHz, CDCl3), δ (ppm): 10.43 (s, 1H), 4.33 (s, 3H), 4.01 (s, 3H)].

Aufarbeitung

  1. filtrationsubsequently filtered from the catalyst
  2. customThe clear solution was evaporated
  3. customto give the crude as a solid which
  4. filtrationAfter filtration
  5. customevaporation 1.77 g (84%) of pure product as off-white crystals
  6. customwere obtained [m.p. 107-108° C.; 1H-NMR (300 MHz, CDCl3), δ (ppm): 10.43 (s, 1H), 4.33 (s, 3H), 4.01 (s, 3H)]

Quellen und Nachweise

ORD-Eintrag
ord-22979babe2784edc98de558f62bb6de2
Quelldatensatz
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07956194B2

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