Sodium hydride → HCID 178444711, Verbindung

HRID 36053

Reaktionsgleichung

Reaktionsgleichung von HRID 36053
[NH:1]1[CH:5]=[N:4][N:3]=[N:2]1.[H-].[Na+].[CH2:8]([N:14]1[C:23]2[C:18](=[CH:19][C:20]([CH3:24])=[CH:21][CH:22]=2)[C:17]([O:25][CH3:26])=[C:16]([CH2:27]Br)[C:15]1=[O:29])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]>CN(C)C=O.C(OC(=O)C)C>[CH2:8]([N:14]1[C:23]2[C:18](=[CH:19][C:20]([CH3:24])=[CH:21][CH:22]=2)[C:17]([O:25][CH3:26])=[C:16]([CH2:27][C:5]2[NH:4][N:3]=[N:2][N:1]=2)[C:15]1=[O:29])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 152333491-hexyl-3-bromomethyl-4-methoxy-6-methyl-2(1H)-quinolinoneHCID 178418441HCID 178418441, Verbindung

Produkt 1

HCID 178444711HCID 178444711, VerbindungAusbeute 52,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of tetrazole (0.17 g) in dimethylformamide (2 ml) at ice-bath temperature under nitrogen was stirred with 60% sodium hydride (0.1 g) for 5 mins and then a solution of 1-hexyl-3-bromomethyl-4-methoxy-6-methyl-2(1H)-quinolinone (Example 14, 0.73 g) in dimethylformamide (8 ml) was added to it. The reaction mixture was stirred at room temperature for 2 hours, diluted with ethylacetate and then washed several times with water. The organic layer was dried and evaporated under reduced pressure. The resulting crude reaction product was chromatographed on silica-gel (30 g). Elution with 10% to 20% ethylacetatedichloromethane gave 1-hexyl-3-(1-tetrazolylmethyl)-4-methoxy-6-methyl-2(1H)-quinolinone (0.37 g). That this compound was obtained was confirmed by the spectral data: MS: m/e 355 (M+); NMR (CDCl3): δ4.18 (s, 3H, OCH3), 5.68 (s, 2H, CH2), 9,14 (s, 1H, CH= ).

Aufarbeitung

  1. washwashed several times with water
  2. customThe organic layer was dried
  3. customevaporated under reduced pressure
  4. customThe resulting crude reaction product
  5. customwas chromatographed on silica-gel (30 g)
  6. washElution with 10% to 20% ethylacetatedichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-9b2ca84c31a3491a8e38aaf5939f1239
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05412104

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