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Hydrochloric Acid → Thieno[2,3-c]pyridine-2-sulfonamide

HRID 569047
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 569047
[OH-].[K+].[S:3]([C:7]1[S:15][C:10]2[CH2:11][NH:12][CH2:13][CH2:14][C:9]=2[CH:8]=1)(=[O:6])(=[O:5])[NH2:4].Cl.C(=O)([O-])[O-].[Na+].[Na+]>O.[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+]>[S:3]([C:7]1[S:15][C:10]2=[CH:11][N:12]=[CH:13][CH:14]=[C:9]2[CH:8]=1)(=[O:5])(=[O:6])[NH2:4]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 14797Potassium HydroxideHCID 201485892-Sulfamoyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine

Produkt 1

HCID 20148577Thieno[2,3-c]pyridine-2-sulfonamideAusbeute 34,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178511488
HCID 178511488, Verbindung
Katalysator
HCID 962WaterLösungsmittel3×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of potassium ferricyanide (76 g, 0.23 mol) in water (400 ml) was added a solution of potassium hydroxide (68 g, 0.113 mol) in water (150 ml), followed by a suspension of 2-sulfamoyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine (10.8 g, 49.5 mmol) in water (50 ml). This mixture was warmed at 80° C. for 4-6 hours. This solution was acidified with concentrated hydrochloric acid and then made basic with saturated sodium carbonate solution. The product was extracted from this solution with ethyl acetate. The ethyl acetate solution was dried over anhydrous sodium sulfate, filtered through a pad of charcoal and evaporated to give 5.5 g of crude product. This material was chromatographed on silica gel and eluted with ethyl acetate to give 3.7 g (34.9% yield) of pure product; m.p. 191°-193° C.

Aufarbeitung

  1. extractionThe product was extracted from this solution with ethyl acetate
  2. dry with materialThe ethyl acetate solution was dried over anhydrous sodium sulfate
  3. filtrationfiltered through a pad of charcoal
  4. customevaporated
  5. customto give 5.5 g of crude product
  6. customThis material was chromatographed on silica gel
  7. washeluted with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-b9fe50193e9a414bafc91b4dead63d8d
Quelldatensatz
uspto-grants-1988_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04731368

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