Sodium Carbonate → HCID 178513361, Verbindung

HRID 1801745

Reaktionsgleichung

Reaktionsgleichung von HRID 1801745
[S:1]([C:5]1[S:9][C:8]([C:10]#[N:11])=[CH:7][CH:6]=1)(=[O:4])(=[O:3])[NH2:2].Cl.[NH2:13][OH:14].C(=O)([O-])[O-].[Na+].[Na+]>O.C(O)C>[OH:14][NH:13][C:10]([C:8]1[S:9][C:5]([S:1](=[O:4])(=[O:3])[NH2:2])=[CH:6][CH:7]=1)=[NH:11]

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 220195265-Cyanothiophene-2-sulfonamide

Produkt 1

HCID 178513361HCID 178513361, VerbindungAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

A stirred mixture of 5-sulfamoyl-thiophene-2-carbonitrile [CAS-No. 519055-65-3] (0.31 g, 1.65 mmol), hydroxylamine hydrochloride (0.23 g, 3.31 mmol) and sodium carbonate (0.175 g, 1.65 mmol) in water (4.6 ml) and ethanol (1 ml) was heated under reflux conditions for 1.5 h. The reaction mixture was poured into water (50 ml) and extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with brine (100 ml), dried (MgSO4) and evaporated. The crude product was purified by flash chromatography on silica gel (ethyl acetate/heptane) and crystallization (ethyl acetate/MeOH/hexane) to yield the title compound (0.21 g, 58%) as a white solid. MS (ISN) 220.1 [(M−H)−]; mp 189° C.

Aufarbeitung

  1. temperaturewas heated under reflux conditions for 1.5 h
  2. extractionextracted with ethyl acetate (3×100 ml)
  3. washThe combined organic layers were washed with brine (100 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe crude product was purified by flash chromatography on silica gel (ethyl acetate/heptane) and crystallization (ethyl acetate/MeOH/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-3a33cba45a3b4b4fa46dc95f771f077e
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349844B2

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