Potassium Hydroxide → [4-(Pyridin-2-ylsulfamoyl)-phenyl]-acetic acid

HRID 858074Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 858074
C([O:3][C:4](=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12](=[O:21])(=[O:20])[NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[CH:8][CH:7]=1)C.[OH-].[K+]>C(O)C>[N:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[NH:13][S:12]([C:9]1[CH:10]=[CH:11][C:6]([CH2:5][C:4]([OH:22])=[O:3])=[CH:7][CH:8]=1)(=[O:20])=[O:21]

Komponenten

4

Edukt 2

HCID 14797Potassium HydroxideHCID 58762849[4-(Pyridin-2-ylsulfamoyl)-phenyl]-acetic acid ethyl ester

Produkt 1

HCID 24267818[4-(Pyridin-2-ylsulfamoyl)-phenyl]-acetic acidAusbeute 65,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of [4-(pyridin-2-ylsulfamoyl)-phenyl]-acetic acid ethyl ester (0.26 g, 0.813 mmol) in absolute ethanol (10 mL) was treated with a 1.0M ethanolic potassium hydroxide solution (2.0 mL, 2.0 mmol). The reaction mixture was heated to reflux under argon for 3.5 h. The reaction mixture was then concentrated in vacuo. The residue was dissolved in water and filtered through celite. The filtrate was acidified to pH=4.5 with a 1.0M aqueous hydrochloric acid solution. The resulting precipitate was collected by filtration, washed with water, and dried in vacuo to afford [4-(pyridin-2-ylsulfamoyl)-phenyl]-acetic acid (155 mg, 65%) as an off white solid; 1H NMR (DMSO-d6, 300 MHz) δH 12.26 (broad s, 1H), 7.96 (d, J=4.4 Hz, 1H), 7.77 (d, J=7.7 Hz, 2H), 7.80 (t, J=7.5 Hz, 1H), 7.37 (d, J=7.7 Hz, 2H), 7.13 (d, J=8.8 Hz, 1H), 6.82 (broad s, 1H), 3.62 (s, 2H); LRMS for C13H12N2O4S (M+H)+ at m/z=293.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux under argon for 3.5 h
  3. concentrationThe reaction mixture was then concentrated in vacuo
  4. dissolutionThe residue was dissolved in water
  5. filtrationfiltered through celite
  6. filtrationThe resulting precipitate was collected by filtration
  7. washwashed with water
  8. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1999cab57aa548be94fb6fc5cbb5e8d5
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07148229B2

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