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Sodium ethoxide → Ethyl 2-ethoxy-5-(4-ethyl-1-piperazinylsulfonyl)nicotinoate

HRID 2229791
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2229791
Cl[C:2]1[N:12]=[CH:11][C:10]([S:13]([N:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH3:23])[CH2:18][CH2:17]2)(=[O:15])=[O:14])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[O-:24][CH2:25][CH3:26].[Na+]>C(O)C>[CH2:25]([O:24][C:2]1[N:12]=[CH:11][C:10]([S:13]([N:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH3:23])[CH2:18][CH2:17]2)(=[O:15])=[O:14])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:26]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 2723922Sodium ethoxideHCID 22052238Ethyl 2-chloro-5-(4-ethyl-1-piperazinylsulfonyl)nicotinoate

Produkt 1

HCID 10109777Ethyl 2-ethoxy-5-(4-ethyl-1-piperazinylsulfonyl)nicotinoateAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A solution of Ethyl 2-chloro-5-(4-ethyl-1-piperazinylsulfonyl)nicotinoate (36.1 g, 0.1 mol) in ethanol (180 mL) was cooled to 10° C. with stirring. Sodium ethoxide (10.2 g, 0.15 mol) was added portionwise keeping the temperature below 20° C. The reaction mixture was then stirred at ambient temperature for 18 hours. The precipitate was filtered off and water (180 mL) added to the filtrate. The filtrate was then heated to 40° C. for 1 hour. Ethanol (180 mL) was then distilled off at ambient pressure and the remaining aqueous solution allowed to cool to ambient temperature. The precipitated product was then filtered off, washed with water and dried under vacuo at 50° C. to afford the title compound (12.6 g, 34%) as a light brown solid. M.p. 66-68° C. δ (CDCl3): 1.04 (3H, t), 1.39 (3H, t), 1.45 (3H, t), 2.41 (2H, q), 2.52 (4H, m), 3.08 (4H, m), 4.38 (2H, q), 2.57 (2H, q), 8.38 (1H, d), 8.61 (1H, d). m/z (Found: 372 [M+H]+, 100%. C16H26N3O5S requires 372.46).

Aufarbeitung

  1. customthe temperature below 20° C
  2. stirringThe reaction mixture was then stirred at ambient temperature for 18 hours
  3. filtrationThe precipitate was filtered off
  4. additionwater (180 mL) added to the filtrate
  5. distillationEthanol (180 mL) was then distilled off at ambient pressure
  6. temperatureto cool to ambient temperature
  7. filtrationThe precipitated product was then filtered off
  8. washwashed with water
  9. customdried under vacuo at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-815a8e438d074844a9ff22a73cda2426
Quelldatensatz
uspto-grants-2002_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06420557B1

Notizen zur Reaktion

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