Stannous chloride dihydrate → 5-Amino-4-(thiazol-4-yl)thiophene-3-carbonitrile

HRID 2098141Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2098141
[N+:1]([C:4]1[S:8][CH:7]=[C:6]([C:9]#[N:10])[C:5]=1[C:11]1[N:12]=[CH:13][S:14][CH:15]=1)([O-])=O.O.O.[Sn](Cl)Cl>C(OCC)(=O)C>[NH2:1][C:4]1[S:8][CH:7]=[C:6]([C:9]#[N:10])[C:5]=1[C:11]1[N:12]=[CH:13][S:14][CH:15]=1

Komponenten

4

Edukt 2

HCID 61436Stannous chloride dihydrateHCID 68754106HCID 68754106, Verbindung

Produkt 1

HCID 687545655-Amino-4-(thiazol-4-yl)thiophene-3-carbonitrileAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 5-nitro-4-(thiazol-4-yl)thiophene-3-carbonitrile (0.071 g, 0.31 mmol) in ethyl acetate (3 mL) was added tin (II) chloride dihydrate (0.29 g, 1.27 mmol). The reaction mixture was heated in an oil bath set at 70° C. under condenser. After 20 min. the mixture was cooled to RT and concentrated under reduced pressure. Purification by flash chromatography (silica, 40:60 ethyl acetate/hexane) gave 5-amino-4-(thiazol-4-yl)thiophene-3-carbonitrile (24 mgs, 38%) Retention time (min)=1.837, method [4], MS (ESI) 208.0 (M+H).

Aufarbeitung

  1. temperatureThe reaction mixture was heated in an oil bath
  2. customset at 70° C. under condenser
  3. concentrationconcentrated under reduced pressure
  4. customPurification by flash chromatography (silica, 40:60 ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-3990b8ea89984688b72f9e138d190cf3
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450363B2

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