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

HRID 1519927Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1519927
[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-b40b15d1c8f849ea9bdfecafab64f37c
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073891B2

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