Sodium Hydroxide → 2-Ethoxy-5-[(4-ethylpiperazino)sulfonyl]nicotinic acid

HRID 348422Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 348422
[CH2:1]([O:3][C:4]1[N:14]=[CH:13][C:12]([S:15]([N:18]2[CH2:23][CH2:22][N:21]([CH2:24][CH3:25])[CH2:20][CH2:19]2)(=[O:17])=[O:16])=[CH:11][C:5]=1[C:6]([O:8]CC)=[O:7])[CH3:2].[OH-].[Na+]>C1(C)C=CC=CC=1.O>[CH2:1]([O:3][C:4]1[N:14]=[CH:13][C:12]([S:15]([N:18]2[CH2:23][CH2:22][N:21]([CH2:24][CH3:25])[CH2:20][CH2:19]2)(=[O:16])=[O:17])=[CH:11][C:5]=1[C:6]([OH:8])=[O:7])[CH3:2]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 10109777Ethyl 2-ethoxy-5-(4-ethyl-1-piperazinylsulfonyl)nicotinoate

Produkt 1

HCID 46689282-Ethoxy-5-[(4-ethylpiperazino)sulfonyl]nicotinic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Ethyl 2-ethoxy-5-(4-ethyl-1-piperazinylsulfonyl)nicotinoate (10.2 g, 0.0275 mol) was dissolved in toluene (50 mL) and a solution of sodium hydroxide (1.1 g, 0.0275 mol) in water (20 mL) added to it. This two phase mixture was then stirred vigorously at ambient temperature overnight. The aqueous phase was separated off and adjusted to pH=5.6 by addition of c. hydrochloric acid. The precipitated product was slurried with ice cooling for 15 minutes, filtered, water washed and dried under vacuo at 50° C. to afford the title compound as an off-white solid. Mpt 206–207° C. δ (CDCl3): 1.25 (3H, t), 1.39 (3H, t), 2.82 (2H, q), 3.03 (4H, m), 3.25 (4H, m), 4.50 (2H, q), 8.25 (1H, d), 8.56 (1H, d). m/z (Found:344 [M+H]+, 100%. C14H22N3O5S requires 344.38).

Aufarbeitung

  1. customThe aqueous phase was separated off
  2. additionadjusted to pH=5.6 by addition of c
  3. waitThe precipitated product was slurried with ice cooling for 15 minutes
  4. filtrationfiltered
  5. washwater washed
  6. customdried under vacuo at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-ea9afc8d3d964727b317a443ec91d048
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176311B2

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