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Dimethyl malonate → HCID 18959456, Verbindung

HRID 1708537
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1708537
Cl[C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[C:5]([Cl:23])=[CH:4][C:3]=1[N+:24]([O-:26])=[O:25].[C:27]([O:34][CH3:35])(=[O:33])[CH2:28][C:29]([O:31][CH3:32])=[O:30].[H-].[Na+].[Cl-].[NH4+]>CN1CCCC1=O>[Cl:23][C:5]1[C:6]([CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[CH:7][C:2]([CH:28]([C:27]([O:34][CH3:35])=[O:33])[C:29]([O:31][CH3:32])=[O:30])=[C:3]([N+:24]([O-:26])=[O:25])[CH:4]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 7943Dimethyl malonateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 18959455HCID 18959455, Verbindung

Produkt 1

HCID 18959456HCID 18959456, VerbindungAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387
N-methyl-2-pyrrolidone
Lösungsmittel

Reaktionsbedingungen

Temperatur
57 °C

Versuchsvorschrift

2,5-Dichloro-4-(2-[4-(t-butoxycarbonyl)-1-piperazinyl]ethyl)-nitrobenzene (5 g, 13 mmol) and dimethyl malonate (3.8 ml, 33 mmol) were stirred in N-methyl pyrrolidone (75 ml), at room temperature under nitrogen, while sodium hydride (1.33 g, 33 mmol, 60% in oil) was added. The reaction mixture was heated to 57° C. for 7 hours. The reaction mixture was cooled and poured into saturated aqueous ammonium chloride solution and extracted twice with ethyl acetate. The combined organic layers were washed with water three times, one time with brine and dried over magnesium sulfate. Evaporation of the solvent in vacuo gave an oil which was chromatographed over flash silica gel with ethyl acetate/hexanes followed by ethyl acetate. The fractions containing the desired product were combined and evaporated to give an oil, 2.5 g, 48% yield. NMR (CDCl3) δ 8.09 (s, 1), 7.45 (s, 1), 5.31 (s, 1), 3.79 (s, 6), 3.43 (m, 4), 2.98 (t, 2), 2.61 (t, 2), 2.47 (m, 4), 1.43 (s, 9).

Aufarbeitung

  1. additionwas added
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted twice with ethyl acetate
  4. washThe combined organic layers were washed with water three times, one time with brine
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the solvent in vacuo
  7. customgave an oil which
  8. customwas chromatographed over flash silica gel with ethyl acetate/hexanes
  9. additionThe fractions containing the desired product
  10. customevaporated
  11. customto give an oil, 2.5 g, 48% yield

Quellen und Nachweise

ORD-Eintrag
ord-af5e83d173f3414387ed51cd5944be6b
Quelldatensatz
uspto-grants-1994_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05359068

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